@Patrick Mulligan adding to @Cesar Castro if your first purchase was $281,500 that would have consumed about $70,375 of $121,087 normal VA benefits limits.

I think self management would be very doable for you and your spouse provided you either buy decent units or get them renovated quickly minimizing the need for time consuming repairs.

Regardless of where you choose to purchase your STR, there could be some upfront and potential time-consuming start up processes.

It's the most susceptible and bottomless aspect of consumer discretionary income.

Bill" and being able to seek local private health care when further than 30 minutes from a VA offered healthcare facilities.

Some real quick items here:VA Loans are for Primary HomesYou can use VA Loans for 1-4 unit properties (House Hacking)VA Loans have 0% downpayment (most of the time)You can have more than 1 VA loan (some people don't know that)VA Loans do carry a "funding fee" which is like a little "tax" to write the loan, but it is waived if you are a disabled veteran.VA Loans do not have PMI (and that's a huge benefit for us)VA Loans also have a very streamlined refinance feature (called a VA IRRRRL) which makes it super easy to refinance if rates were to fall (hopefully that will occur in the future)VA Loans can also be used by a surviving spouse.The VA may not give us the best health benefits but they can certainly get us into debt!

Note many of your items in this project are not related to health and safety.  

Depending on the health of your parents, waiting until a death, although grim, could wipe out significant amounts of capital gains. 

It makes it easier for bad actors to commit fraud on their application.The article does say "The report will be made available to landlords at no cost and will have to be prepared by a consumer credit reporting agency" but landlords should be able to verify that somehow and ensure there have been no changes.

I ended up leaving the partnership due to venturing off to focus on my startup but no bad blood.Recently I’ve been contacted by the father of one of the partners and he’s having some health issues but in the midst of it all the property is having some foundation issues.