Seeking advice on how to spend $250k...

[Jake Young]

Ok, so I don't have the money yet but I will soon as I finish this house and pull a mortgage on it and I want to do this next step 'right'...

Backstory:  I'm 43 born and raised in AK and have been working in construction for the last 10 years. Before that I was a production logger among other things.

When I was 23 my Canadian wife and I bought first house for $63k in a small logging/mining town in BC. The next year they announced a ski hill development and mining operation.  We sold house 1.5 years later for $127k. (then they sold it for $154k, then 2008 hit)

A week after selling that house I read Rich Dad book which basically said I should not have sold UNLESS I could parlay that money out with sound strategy, which I think I did.

I turned around and bought a raw lot in same town for $20k (it was cheap due to setback restrictions for septic and well). we ended up installing tanks that need to be pumped out every 6 months, no big deal.  Build small 24' x 24' cabin on it rents for $800/mo now for last 13 years. And now worth $200k ish. Never gonna sell. If I could throw some capital at it and build 'real house' it would be worth $600k

Also at same time bought small chunk on the beach in Nicaragua for $40k split with 2 other people. General bad idea. No plans for future. languishing...

Also bought piece of  swamp land in lucrative market ski town market here in Alaska. 1/6 acre for $60k.  Put 50% on land (I was now broke again) then borrowed another $100k to develop land.  Moved small cabin there, drilled well etc.  Whole house done for $107k. Now worth $600k

Whew!  this was all back in 2003-20010

Next stage, borrowed on equity in that house and bought raw land in Hawaii for $16k.  (accidental bottom of market yay!) Now lots are going for $50k...

In the last 5 years I have out of pocket put in $50k in dirt work, septic, slab, framed first floor.  This last month I finally procured  $100k hello to finish, 3 bed, 2 bath will be worth $600ish when done (assuming market does not tank but prices have definitely been coming down)

My plan: finish this house by December 2023 only owing $100k on it. Pull as mortgage as much as possible $350k, pay the $100k off and have $250k to take this **** show to the next level!

My skills:  'journeyman carpenter' turned 'commercial superintendent' turned 'custom home GC' now purposefully downsized to individual worker building decks and small Renos and the like. Way less stress for more money and flexible hours.  (I ski a couple hours every day in the winter ;)

My options:

Buy another lot in Hawaii for $50k, build house for $150k that is worth $600k again (rent or sell?) 8 month turnaround after permits in place. repeat...

Or go local back to Alaska and use $250k parlayed out into multiple rental units?  

or downpayment on new to me house for $700k and rent this one Im in? The rental market is hot, hot, hot in this ski town. everyone does airbnb, long terms are hard to come by.

or, or, or

Question: if I were to buy a house for a renter, does the bank take the as of yet rental income into consideration of debt to income ratio?

so in theory I could like 10% down on 4-5 houses at once ($3-400k range in Anchorage). ?

??

Thanks!