In terms of negotiating a price and management contract, which side of the bet would you prefer to be on?  

@Gregory Cudzilo market in Virginia Beach right now is tough with most market properties selling in days above list, best bet would be to have that conversation with your agent up front so they know what they are in for and can better advise you on the current market in the Hampton roads region

Rent adjustment may be a consideration compared to the last lease agreement, but that can be changed over time, a long term tenant is more important than that potential 50 dollar difference per month right now.

That’s the best bet.

SD market is tough for cash flow, at least when you initially purchase the home.Your best bet is a live in flip / house hack, meaning you buy a house in need of some love in a nice neighborhood at a discount, fix it up and then house hack.  

Generally, 20% down, 5%interest amortization over 20 years, rate is adjustable after 5 years.

Your best bet is to buy a multifamily, live in one unit for a year, and rent out the other units. 

Be it adjusting the purchase price, improving the ARV, changing the financing, etc.

IMO your options are: (1) look in less expensive markets where your dollar goes further, (2) invest in a different asset type, (3) invest with someone else / partner on a deal, (4) wait for prices to adjust, if it happens... personally, I would expect to see some distressed sellers who are going to be taken out by the eviction moratoriums due to abusive tenants - MA is brutal when it comes to the super-progressive lawmakers who think free rent w/o aid to landlords is perfectly acceptable... but I digress.

If you plan on using your VA loan (which I highly recommend for a house-hack) you have a few options: Your best bet would be getting a full time job lined up immediately after your EAS.