I suspect that until I get both investment properties fully leased that my debt to income ratio will be too high. 

Any feedback on this deal is highly welcomed. 

If you don't already own a primary residence, I highly recommend researching the investment strategy of house hacking.

Partner Driven was interested in the N Deerview Dr deal in Lake Villa, IL, due to its high profit potential.

Partner Driven was interested in the N Deerview Dr deal in Lake Villa, IL, due to its high profit potential.

Partner Driven was interested in the N Deerview Dr deal in Lake Villa, IL, due to its high profit potential.

We are now disabled and maintaining the land (in city limits) is becoming too much, AND property tax values are TOO high, due to a few lots that keep selling and owners later finding out new fema guidelines have made lots unbuildable.

Being in Texas with a lot of drill rod, if you have a welding friend with a high lift, I would look to do Canopy parking. 

If Oregon is of interest there is a significantly lower entry price per door with somewhat comparable CA returns, certainly a luxury STR would perform and be manageable with a local team. 

Kentucky's market is one of the few where such profitable returns are still possible.