If you need financial help, ask under the "Finance, Tax, and Legal" forum.

So, many landlords legally "bribe" these S8 tenants to move into these Neighborhoods/Properties with free appliances, TVs and internet.

Needless to say, many parties are involved, and they all need to be established and verified, or your business will suffer greatly. 

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

There are some legal considerations as well as practical considerations 1.  

There are actually THREE kinds of subject to transactions1- subject to existing mortgage without lender approval2- subject to existing mortgage WITH lender approval3- subject to existing mortgage as part of a seller financed wrap around mortgage.with #1 and #3 it’s in everyone’s interest to utilize a third party servicer, who collects and then distributes payments.  

Check out Every Landlord's Legal Guide by NOLO.

One question that you may not want to post here for legal reasons, is how much are you paying your PMC?

i invest via 50/50 partnerships. i find/coordinate/manage the deal, and my partner brings the capital to the deal & approves large expenses. on their end, it's just about as hands-off as investing in a syndication, but they get to be one of just two main 50/50 decision-makers. and when there are just two parties involved in a deal like this, vs it being diluted across tons of investors, i find it's also possible for the capital partner to see much higher returns. when it comes to teaming up in real estate i'm much more relationship-based and less transactional. i'd rather do fewer very high-quality, carefully selected deals, each with just one capital partner, so that i can really serve that person's best interests and get us amazing results, vs. doing a bunch of diluted deals. i also feel a lot of syndicators out there are newer to the game, lack experience, haven't used their own money enough, and don't use their investors' dollars with enough caution. it gives the high quality syndicators a bad name.

@Ryan Swan, funny you say that, I just used all of my votes on that one feature last week, which kind of sucks because I wouldn't consider that an "enhancement" as much as just a total whiff on Buildium's part.  I