No major roads between the house and the beach?

I still do have a mortgage on that house, so planning on getting those monthly payments to pay existing mortgage.

@Bryce KennebeckKudos to you for operating a STR house hack!

There are a few houses on a street where I already have a house.

The house itself is livable.

You can get the rest of their entitlement by multiplying it by 4$100,250 * 4 = $401,000They can buy a house up to $401K and still use 100% of VA entitlementsBonus: If they want to buy a more expensive home, they have to put 25% down on the difference of the home and the entitlementExample: Seller wants to buy a $601,000 house$601,000 - $401,000 = $200,000 (difference)Down payment = $200,000 * 25% = $50K% down on home = $50K/ $600K = 8.3% down payment

How do you keep track of insurances expirations, taxes dates, equity growth per house, rental growth in your area ? 

We used to have in-house inspectors but it was hard to scale and with our heavies season being that of summer months, at 1000+ units we weren't able to hire enough inspectors for the last day of month move outs and first day of month move ins and then still keep them fully-employed in our slower season in fall/winter.

if the building cashflows really well ... it wouldn't be a big deal to use a loan for dp right...at 10% down for lower income housing I don't have much money and I think that this is the best way to get multi-family management experience to meet hud loan requirements in the future which Have the lowest Down payment options.Am I overthinking it?

We got a shaman to come in and it turned out there were 4 ghosts including the previous owner who had passed away there and the original owner of the house who had died there during child birth.