I'm currently looking for an investor friendly Title Company and Agent out in Arizona.Wanting to create a relationship where both parties can win!

The bad part is the entire 95 acres will be a dust hole for the next 2 years starting Q1/2022. 

The only difficult part I see with doing both (as a beginner) is funding, the more you invest in your 401k and Roth IRA, the less you have for those down payments and ways of financing

The more important part is knowing what numbers to put in the spreadsheet.

. § 44–14–80 was modified to provide for an automatic reverter of title to land described in a security deed after seven years from the maturity date of the debt secured thereby or 20 years if the parties so expressly agree in writing in the security deed.”

I was able to move into the house once I got it more comfortable and the best part is my girlfriend helps pay the mortgage!

If I had partners and was paying for a service to a 3rd party anyway, avoiding SE taxes wouldn't be my focus so I would probably try to do it.  

If an investor is looking for conservative plays with monthly cash flow, then 'thank you next' (unless they are ALSO open to development plays like this...)4.

You have to have a strategy to prevent these things...and I would think you don't always want to leave that to third party property management, that you want to do that yourself.Probably in most cases if you're just going a few times a year, and you're going in peak season, probably cheaper in the long run to rent hotel rooms or other STR vs buying one if that is your motivation.

I would be paying for it in cash, and my rough but conservative calculations of renting out just 10 days a month net me a positive cash flow of between $475-$531.