Just went and looked at a potential deal that is the first of its kind as far as my investing career goes.

Single family home on a great street in a B neighborhood, historic city. There are some rough parts of this neighborhood, but this block and the blocks around it are regarded as the best in the neighborhood and have been since this city was established in the late 1800s. It is right around the corner from 3 historic 100+ year old mansions that have nearby streets named after the families that built them.

It is a 2 story home with a full livable basement (3 levels total). We have 3 total kitchens, one on each level. Basement = 3 rooms, main floor = 3 rooms, top floor = 2 rooms. 1 full bathroom on each level. All rooms are pretty basic around 10'X12'. Only difference is top 2 have walk in closets w/ slightly more sqft and basement rooms have lower ceilings.

Currently, the rooms are being rented individually as a clean and sober home. No medicare, government funding, licensed employees, or any of that. They are just renting by room privately and advertise as a sober home (from what I understand).

The condition is very good. The entire home was gutted and remodeled 6 years ago. Electrical and plumbing is the same as new construction, roof is 6 years old and good condition, appliances are all in acceptable 6 year old condition. Some are even better.

It is in the appropriate zone to be converted to a triplex, if you locked the doors to the stairs each level would be completely private. Each level already has their own entrance from outside as well.

That about sums it up. 8 bed, 3 bath home with 3 kitchens.

My questions for the people who have seen/bought something like this:

What are the pros/cons? I can see the cash flow this will bring in and have multiple ways I can approach it. My main concern is my exit strategy. What troubles might I run into trying to sell a SF home with 3 kitchens? Trying to convert it to a duplex/triplex? Other than the extra work involved, what problems can arise from individually renting to 8 roommates?

Thanks in advance for all your help!