You can us a VA Loan to buy a 1-4 unit property as long as you live in one of the units. 

i will answer your last questions first. 

I think holding is a great long term plan.

In the last 5 years, we've invested over $300k of savings toward down payments and rehabs. 

As with all regions, the Oregon Coasts' counties and cities are tightening their rules (and quantities of allowable vacation rentals) and there are a few adjustments to last year's regulatory landscape.

Even those with long track records are strugggling to raise $ as well as break even on deals 

Actually the last time I opened it it automatically forwarded me to the new web page and until that happened I hadn't realized that was what had happened.   

They also, last minute, changed an 8 bed Fourplex to a 6 bed.

My uncle has done 84 percent for the last 14 consecutive years (these numbers can be proven  and have been well documented) .

Caulk should last five years.