Spring may be better but I was unable to sell a cheap house in October for 5% off of “market value” and only sold a $600k home in January by listing it for $580k and I still only got one offer. ($150k down, 5 year seller financing.) my point being you may get $20-$40k more in a year if you don’t need to sell. 

First step is to figure out how to buy the land (if it is even for sale); I have the name of the owner from the tax rolls, so I think I will start there. 

I’m a family man also with a couple teenage kids,, I feel if I can get more properties now, it’ll help my kids to own & live in one of those properties that they wouldn’t be able to afford 1,2,3, or 4 decades from now when I am gone..

If you’re worried about guest perception, you can always roll some of the cost into the nightly rate instead.

Happy to connect and share whatever resources I can to help you get the ball rolling this year! 

If the goal is greater flexibility, consider rolling over the SDIRA into a Solo 401(k) for more investment options.

I pay a neighbor's kid $10 a week to roll 2 cans down to the street and back. 

MBD meaning after tax 401k contributions rolled over into a Roth IRA. 

Would love some guidance on best first step to get things rolling.

These products allow you to purchase a home that may need some work and roll the renovation costs into your mortgage.