I a factoring in the replacement of the AC unit and potentially the water heater, and the cosmetic thins (I would do myself) to get it to rentable standard.

There's a lot of timing to consider, and honestly, this potential first cost segregation will be a learning experience for us. 

Hey Account Closed - I highly suggest  using a renovation loan and house hacking a multi-family if that is possible with your current life circumstances.The 203k and homestyle renovation loans are just amazing products and drastically help you reduce your risk, in my opinion, because you are able to leverage the cost of the entire renovation with such a low down payment loan.We work with a lot of clients who use these products in Chicago, and no matter what, in the long term, they gain great equity.If you aren't able to house hack - the process is essentially the same, but just with more money down with hard money or conventional construction loan.

Lesson learned is to pay more to get into a nicer area (B neighborhood) with more reliable tenants to avoid the vacancy risks, but again, if we can just get the 2nd unit filled we will finally have stable cash flow.

Because their investments do NOT have a higher enough ROI adjusted for risk.  

Wish you the best.If I was you, first step is evaluating costs associated with doing MTR and comparing with potential rental income to see if it makes sense to do LTR or MTR.

So, I'm interested in the Kissimmee Florida area for a potential retirement home.

Section 8 is best used as a risk mitigation tool for properties in super low income, high crime areas.

Are you looking to sell a flip or are you in need of funding for a potential flip?

It minimized vacancy risks and kept things amicable.Address Tenant Concerns CalmlyI’ve found that tenants often feel more cooperative when they understand the landlord’s perspective.