You or you brother may find out you dislike house hacking.I'd start understanding your budget and seeing what areas of the city you can afford.

I find when people dislike their Section 8 tenants, it's because they aren't screening well. 

I've gone most of my life lacking trust in wealthy people, and mostly just disliking them, and have only just recently begun to understand why I was wrong. 

There are TONS of discussion threads about this here on BP, just put Section 8 into the search query.Very high level:I love it for the guaranteed rent, higher rents (sometimes), long tenancies, added accountability for tenants through the housing authority and enormous supply/demand gap (there is a lot more demand than supply in most places for s8 housing).People often dislike it because the housing authority can be tough to deal with (this varies widely from one county to the next because it's administered locally), rents can be too low in certain areas (usually A areas) and there is a perception that the tenants are awful.I've found that extremely thorough screening negates the last issue.

I agree with Brian here - there are so so so many posts on Section 8 and people have very passionate opinions on the topic.Very high level:I love it for the guaranteed rent, higher rents (sometimes), long tenancies, added accountability for tenants through the housing authority and enormous supply/demand gap (there is a lot more demand than supply in most places for s8 housing).People often dislike it because the housing authority can be tough to deal with (this varies widely from one county to the next because it's administered locally), rents can be too low in certain areas (usually A areas) and there is a perception that the tenants are awful.I've found that extremely thorough screening negates the last issue. 

Spend some time with a glass of wine looking at the ceiling to understand yourself - your strengths/weaknesses, likes/dislikes, geographical and type preferences of real estate investing. 

We try to make it as painless as possible, but all those years ago when I was a tenant I disliked it too.

If you dislike the business, but want the benefits of real estate, consider investing that $200K into syndications, REITs or some other passive real estate investment.

Jumping into paying for software before you truly know your needs, likes, and dislikes for software is challenging.

Quote from @David Dachtera: My biggest kitchen peeves are:- Stove in a corner- Stove on an inside wall- Stove on an outside wall, but no range hood or the range hood is not vented to the outside* Heavy Sigh * Just curious -- why do you dislike a stove on an inside wall?