Should I find a few buyers before I go out trying to find sellers, or should I start with sellers, then look for sellers directly or bring it to other wholesalers?

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.

Curious though if you have other paras or intend to bring on more folks on the legal side since most the others are ops and CPAs? 

A ring camera will give you the evidence you need to stop a potential party or when people bring in too many guests over night.

I average about $2000 a month in cashflow on the current rental property, and the new property would bring in around $3500 in gross revenue.

The triplex is occupied and currently bringing in positive cash flow.

If this doesnt fit with your goals, it's time to bring on a partner.

Key items to rehab on the second home to bring the property value up for the refi, determining which lenders/servicing companies will be favorable, Identifying good properties to invest in altogether.

I don't have much experience dealing with Section 8 and I wonder whether there's a risk of bringing attention to a non-conforming rental to the Section 8 authorities. 

What skills do you bring that are superior to those you want to raise money from?