I have restrictions on both that do not allow any sort of "vacation rentals" and a minimum 6 month lease requirement.

(big loss yes but compared to the upside, I dont know) but lets say it takes 9 months to build (leaving me 3 months left on my loan, which my lender due to covid has an extension clause) if I drew all the money at once my yearly interest would be approx. 180k)...Lets say there a supply issue and it hold me back 5 months over the year which costs me 15k a month.  

To combine the two into a land purchase and construction loan you need to demonstrate on paper exactly what you plan to build and that the planning desk allows this without a conditional use permit/hearings/delays/neighbor complaints tying you up to wait 24 months to start.

I saw company a few months ago.. 

I would prefer to self manage to avoid the high poperty management fees (I think its around 10% + 1 month leasing fee, etc.) and I also worry that the property manager will likely not be as dilligent in finding high quality affordable vendors, etc.I see 4 major pieces of work1) Tenant finding: I feel comfortable doing this remotely.

(Rent Zestimate®: $1,599 and I am collecting $600/month) Can this be considered a "Not Rented for Profit" rental property/agreement?

I'd then repeat this process every 12-18 months until I had a reason to stop.Concurrently I'd be trying to increase my W-2, or 1099, income as much as possible, as soon as possible.

My guess is if you had to evict them, the deposit was used for unpaid rent.For future, if you have the tenant pay the water directly (and it is tied to the house), get a copy of the bill either every month or every couple of months to make sure it is paid up. 

I recently had to use a local laundromat for a couple of months and loved the option of using a designated laundry app to pay.

Property 1: Single familyWorth 20 - 30kNo debtProperty 2:3 familyWorth roughly 60k18k left on a 5 year owner financed deal with about 33 months remainingThe values are rough estimates.