Just one month of vacancy a year takes away any cashflow you would have. 

When you build enough capital/assets/net worth to afford a reasonable monthly cushion you can see if the lifestyle of a full time investor is something you’d want to pursue.  

I think I will not let him make this upgrade as a 5 year payoff would require over $100/month additional rent.  

If we had hundreds of loans out, we’d have enough monthly income to aggregate the payments into additional loans—but we don’t.If you do this, your note will have to have a compounding clause in it, provided by your lending attorney.

Every month you receive cashflow from rental income.

What you spent on the land/lots can go towards your down payment and, if you've owned the land for more than 6 months, you can use the value of the property toward the cash injection requirement.

Set a goal to buy your first property within X months.

I have yet to do any training on Arive and been using it for 6 months.

For those with STRs there, what is occupancy rate and is there still some demand in off months or are off months just dead?

Taking the loss now is preferable to paying out monthly for the privilege of being a landlord.