I am currently playing a Rogue who is the party's 'healer'.

I put that in quotes because he's taken a background of Back Alley Doctor, meaning he has the Risky Surgery feat which says:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

We're only 1st level right now, but when I reach 2nd level, I'm considering taking the Assurance feat, which says:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

At 2nd level, assuming I improve my Medicine to Expert, my bonus for medicine checks would 4 (for Expert) + 2 (level) + 3 (Wisdom) = +9.

Given that a successful Treat Wounds check only requires me to pass a DC15 check, it seems that by using Assurance I can always guarantee myself a success since my result would default to 16 (as I only get the proficiency bonus, which is level + T/E/M/L, for Assurance). Could I combine this with Risky Surgery's benefit which stipulates that a regular success becomes a critical success?

Additionally, is it correct to assume that I can't get Risky Surgery's +2 bonus since Assurance bars any other bonuses?

I am currently playing a Rogue who is the party's 'healer'.

I put that in quotes because he's taken a background of Back Alley Doctor, meaning he has the Risky Surgery feat which says:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

We're only 1st level right now, but when I reach 2nd level, I'm considering taking the Assurance feat, which says:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

At 2nd level, assuming I improve my Medicine to Expert, my bonus for medicine checks would 4 (for Expert) + 2 (level) + 3 (Wisdom) = +9.

Given that a successful Treat Wounds check only requires me to pass a DC15 check, it seems that by using Assurance I can always guarantee myself a success since my result would default to 19. Could I combine this with Risky Surgery's benefit which stipulates that a regular success becomes a critical success?

Additionally, is it correct to assume that I can't get Risky Surgery's +2 bonus since Assurance bars any other bonuses?

I am currently playing a Rogue who is the party's 'healer'.

I put that in quotes because he's taken a background of Back Alley Doctor, meaning he has the Risky Surgery feat which says:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

We're only 1st level right now, but when I reach 2nd level, I'm considering taking the Assurance feat, which says:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

At 2nd level, assuming I improve my Medicine to Expert, my bonus for medicine checks would 4 (for Expert) + 2 (level) + 3 (Wisdom) = +9.

Given that a successful Treat Wounds check only requires me to pass a DC15 check, it seems that by using Assurance I can always guarantee myself a success since my result would default to 19. Could I combine this with Risky Surgery's benefit which stipulates that a regular success becomes a critical success?

Additionally, is it correct to assume that I can't get Risky Surgery's +2 bonus since Assurance bars any other bonuses?

I am currently playing a Rogue who is the party's 'healer'.

I put that in quotes because he's taken a background of Back Alley Doctor, meaning he has the Risky Surgery feat which says:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

We're only 1st level right now, but when I reach 2nd level, I'm considering taking the Assurance feat, which says:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

At 2nd level, assuming I improve my Medicine to Expert, my bonus for medicine checks would 4 (for Expert) + 2 (level) + 3 (Wisdom) = +9.

Given that a successful Treat Wounds check only requires me to pass a DC15 check, it seems that by using Assurance I can always guarantee myself a success since my result would default to 16 (as I only get the proficiency bonus, which is level + T/E/M/L, for Assurance). Could I combine this with Risky Surgery's benefit which stipulates that a regular success becomes a critical success?

Additionally, is it correct to assume that I can't get Risky Surgery's +2 bonus since Assurance bars any other bonuses?