I would speak with lender(s) and check their attitude about moving title to one or more LLCs.

We are at a 65-70 occupancy rate and you can still get on the sand (condo) for affordable rates. 

My homes are from the 70's and are outdated, yours looks a lot newer.

If you plan to use a VA loan, then it means some kind of house hack.If the house is 100 years old, then the maintenance costs will be significantly different than a house that is 10 years old.If the house is coastal, the insurance costs are probably low.Without details about the property, the numbers don't mean much.

$20k is a grain of sand on the beach on a $450k house (20% down is $90k).Are couples saving $90k for a starter, or are the bulk of these going to investors.They ought to make the grants $400k to get to a reasonably priced starter home (IMO w/o running any local numbers--just asking).Are you wages that high locally?

Thank you for the feedback @Bill S. and @Scott Trench.

You could use AirDNA to get an idea on #'s and occupancy rates.

In your 50's and 60's you realize you aren't 20 anymore and really need to enjoy the fruits of your labor more and travel while you can.

@Thomas Hoyla I admire your ambition but if you came to me I would tell you to pound sand.  

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