In-town, most properties don't meet the density/saturation requirement.

Nice to meet you.

You can have as many DSCR loans as you like as long as you meet the requirements for the product, there is no ceiling to your growth.

Have you tried attending your local REIA's and real estate meet-up groups?

Meet people and network with them.

This being said, I don't believe we'll be able to meet the income requirements to qualify for a conventional.This leads me to believe hard money or private lender is more the only option to get my foot in the door, use my business to make repairs at very good rates, build some equity then refi once the balloon is due. 

That said, hiring lawyers to write contracts, background and credit checks on strangers that already look nefarious may just add to the stress that we're trying to get rid of.

You're likely better off attending your local REI meet-up to see if you can find an investor who has house-hacked or is currently house-hacking their primary home.

•Likely, the new property wouldn’t be cashflow positive due to the market conditions.2.Upgrade to a Bigger Property and Sell•Sell our current home and move into a larger house to better meet our family’s needs.• Use some equity from the sale to make this transition smoother.I’m torn between maintaining our current home as an asset and buying  a new smaller house to use as a rental after we move back in versus simplifying and focusing on a single upgraded property Considering factors like market trends, potential equity growth, and quality of life, which path do you think would be most beneficial?

It sounds like they have been paying, maybe talking to them about your concerns can help them better meet your expectations.