Was wondering if this is a common situation with underwriting VA cash-outs. 

Prices east of Worcester towards Boston have become untouchable for the "common folk," and first time homebuyers in the Metro-Boston area are being pushed as far west as Worcester.We made about 15 offers before we got a bite on a 4 bedroom, 2 bathroom, 1600 sqft home in the Webster Square area of Worcester.

It’s not common but it does happen.

Multis / rentals are not common, and in demand.

Any tips on finding properties, researching the market, areas to avoid, common rookie mistakes, ANYTHING!

You had a very common problem (I've had it too) and the best thing you can do is exactly what you did: get quotes and then get it repaired. 

In general I don't think they matter too much, however, against common wisdom, I had to change the name of the last cabin I purchased.  

@Gino GonzalesAcquisition fees are typical (1%-3%) with larger multifamily projects and very common with syndication deals.

Things such as;keeping hand sanitizer stocked in multiple locations in the unitSanitizing common touch points such as door knobs, light switches, shower knobs, etc.Keeping hand soap stocked at sink locations....And there are many more hereI think if you're proactive in things like these, when other owners may not be, it will make you're listing look all that much better.All the best!!

The only common scenario where we’d recommend buying a condo as an investment is if it’s going to improve your life in some way (you plan on retiring there in the future, a kid will be moving in the area in a few years for school, etc.).