Not all VA loans are owner-occupied as the VA gives you an allotment so you can have multiple properties with VA loans depending on what they clear you for.

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

Quote from @Aaron Letzeiser: Quote from @Mohit Gupta: @Steven Toth I was actually able to find multiple carriers who would insure for a slightly higher premium, which I am happy to pay.

Since you are splicing multiple pictures, why not show a good one of the game room and other other key parts of the house instead of all of the game room?

When we follow up it takes multiple business days and sometimes more than a week to get a response. 

Similar for bathrooms if virtually all are multi bathroom but you find a single bathroom, making it multi bathroom via new construction could be a value add.There are more sophisticated value adds such as add multiple adus via bonus density program.  

And I may get multiple bids for the same work, like multiple paint bids, multiple roof bids, multiple flooring bids, etc.

PS before the hedge funds jumped in about 2011 to 2012 I was an activce courthouse buyer in Henry county and a few of the counties on the north side of Atl metro so been to many of the  auctions having them all on one day is a cluster .. you have multiple criers crying sales simultainously it can be hard to follow but you can also squeeze out one that folks missed.. we did quite well until the hedge funds knocked us little guys out of the area..

You can have multiple conventional mortgages and have a great credit score as long as you don't pay late or get too close to the maximum debt to income ratio.

Is this something you have done multiple times?