I think you should start by understanding what it is your investors want out of the deal, analyze how the returns compare to traditional investments, and then see where you fit into this deal. 

Lenders or investors who have short lock up periods but have years of experience feeding their business with new capital would give me more comfort but anyone who is just starting and is promising a rate of return or return of capital in a set period of time would be alarming because they very well could be reliant on fresh capital to make good on that promise and that usually ends poorly.

You started by saying that you have Local bank relationship. 

I'll start there! 

Adding the 1 & 2 bed option is a great start, have you looked at pricing and dropping it further than your peers?

Started the process on 1 house in Cape Coral Nov. of 2021. 

From there you can start to identify what you are looking for.Where do you land on the follow spectrums:Cash flow and AppreciationLong term or Short term needs (waiting for growth vs get out of my W2 now)Long term rentals, Mid term rentals, Short term rentalsBuying close to home or coast to coastSelf manage or hire a PMIf you can narrow in on those, you essentially have your buy box. 

We have renters there now and they cover the mortgage with a bit of cash flow ($100/month), but the property is going to need some more major updates (windows, roof, HVAC, siding) within the next 5 years as they are starting to be at the end of their useful lives.We would like to pay off our primary residence as quickly as possible to “free us” from mortgage payments on our primary residence.My questions are below:1.

Kid in college and one starting to drive   blah blah blah.I'm sure there are numerous places to cut money for sure. 

I've been going about as long as you have and things are starting to come together and happen for me here in Sacramento.