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

I’m interested in house hacking as a potential solution.Should I:Keep saving and wait?

But he's also not the only owner in that company.

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

If you have a solid track record, high reserves, you should be able to get 65% LTV on a non-owner occupied property without any credit checks or an appraisal. 

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?

Look into home owners insurance and what types of warranties do your appliances have to keep them covered as they don't make stuff like they used to.

I don’t want to see you end up as a mom and pop owner with a facility that is under performing and causes a lot of headache for you.  

So your clients who are selling their condos end up buying a house hackable property afterwards?