@Catherine Javier If you find the property is more of a liability to you and ultimately decide to sell, the 1031 exchange would probably be the best way to take advantage of using the tax and find something with a greater growth potential.

At least this next potential home is only a single story so I cant fall as far. 

Consider what questions the potential mentor may ask and how you would answer.

We still see 1% deals here that bring positive cash flow and have potential for appreciation. 

You can use Airdna & other STR estimator tools to get data on potential income/vacancy based on your location and property size. 

You would want to know if anything was ever built on the land (maybe a house burned down) because if there was a house then you would have potentially buried septic or oil.Buying and holding a lot for the future with topographical issues is only worth it if the price is negligible IMO.

The trade-off is losing out on potential growth from a reinvested 1031 exchange, but if you’re thinking about a HELOC later to invest again, this could bridge the gap.What I’d do in your shoes:If it were me, I’d run the numbers on a worst-case scenario for each option.

We are looking into houses on the lower end of the scale at first to get started for a "low risk" (we could pay mortgage out of pocket no problem even if property is vacant for 30 years) house that will give us the experience we need as rental home landlords - and I am looking down the road at potential investment ideas to keep this thing rolling.

Reasoning for asking this is that it could potentially be a beneficial long play on acquiring a property through assumption, and as we go down in interest rates, utilize this monetary benefit to refi as it comes at a mere .5%.

A lot of people travel with pets so charging an extra fee can make up for potential damage plus you expose your property to a broader market that can help with bookings.