Since I'm really busy with my job, I've been strongly considering paying off each one aggressively, which would increase cash flow by 2k which would be similar to owning another 5 units, but without the headache of 5 more tenants and the issues that inevitably arise with owning more properties. 

A handyman, hvac usually, painter, lawn guy...Tossing out numbers to give you estimates;I strongly do not recommend new folks flipping buy a junker 2/1, and expect to punch it out to a 3/2!!! 

Several of my Section 8 tenants are in my Top 20 list of worst tenants (out of thousands) and left owing $10,000 or more due to unpaid rent, cleaning, and repairs.I have strong feelings about people that stay on the government teat long-term, but I'll leave you to form your own opinions.

@Jason Sung, You've got some very strong things that point to demonstrating your intent including1.

Currently, I live in Hawaii, house hacking my own property, and am looking to expand into out-of-state long-term rentals.My goals now are to master the art of wholesaling, continue raising private money, and build a strong portfolio of long-term rentals.

If you have commercial experience and are an excellent asset manager (managing the property manager, driving revenue, reducing expenses,  managing GCs)You wont just provide value to a sponsorYou will be highly sought-after after by sponsorship groups.The ones worth their salt know how incredibly valuable a strong asset manager is (and how much work it takes)So if you can bring that skillset, I have a feeling it won't take long for you to find a sponsorship team. 

It’s great that you’re stepping into real estate with such a strong background in renovations and custom home building—that’s a huge asset.

I wish people could pause and listen to how foolish they sound sometimes when they have strong opinions about how somethings are so wrong on the one hand, but then on the other hand, they do the same thing only in a slightly different way.

If you'll be cash flowing strong, there might be some room there to pul some money out and use it for a downpayment for another house.  

In the future I strongly suggest a similar pricing strategy where you list lower than what the comps come in at.