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Need Advice. Military Officer looking to buy third house.

TL;DR: Should I buy a third house or not?

Hello everyone. 32/M with 13 years in the military. Military income is $115k/yr with $40k untaxed every year. Sometimes $65k untaxed during heavy deployments. Looking to buy a third house in my area.

Background: All homes in the Florida Panhandle, couple miles from the beach. No debt besides mortgage and AMEX 2 year personal loan ($6k, 0% INT).

Assets: Home 1: $70k in equity. (purchased 1/16, refinanced out of VA loan this week (Owe $207k, mortgage ~$1200/mo, 3.25% INT). I rent it short term the six months of every year (I deploy a lot) Income last year: $29k before mortgage payments.

Home 2: Co-owned by myself and business partner(Owe $134k, worth $170k, $950/mo, 5% INT) Short term rental: Rented 75% in off-season, 90% in season. First year, but even through COVID, we haven't paid a mortgage payment yet. If I do, it will be half due to partnership.

Home 3: Potential ~$420k custom built home on the water (VA Loan, 0% down) on the water. My dream home we will build and live in. ($2,100 mortgage). After land and build at $150/sq ft we will have around $30k in equity if we do it right. Fiance makes $55k with $10k balance on car loan (3%).

HURRICANE INSURANCE ON ALL PROPERTIES

$40k in cash $50-80k (#COVID) in stock $100k in ROTH IRAs 50% Pension when I retire in 8 years.

Plan is to buy the third home, live in it and rent out home 2 full time. If rented at 65% for $125/nt after expenses I would net $7k-9k. Brand new roof being installed this month so I won't have any major overhead unless something goes very south. New AC planned in 2-3 years.

I can afford the mortgage on the new home, and realistically if I didn't invest anything, I could afford all three mortgages and bills indefinitely but it would suck... I'm putting about 30% of my income away into retirement funds each month.

Question: Am I stretching myself too thin or have I thought about this enough and I'm just being a worry wart? The only upcoming expenses I have is a nice ring and wedding which will be funded by us because we are way better off than any of our immediate family and wouldn't put that burden on them.

submitted by /u/three8sixer
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source https://www.reddit.com/r/RealEstate/comments/gb9iil/need_advice_military_officer_looking_to_buy_third/
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