What's the monthly HOA fee and do they allow STR?

The condo market is decent in Frederick, however the HOA fees will kill your cash flow.

Utilities are paid entirely by the tenants (except HOA).

I currently have two townhouses that I rent, but I’m looking to expand into multi families to avoid more HOA fees.  

when you say annual assessment, are you talking about the taxes or an HOA fee? 

Literally, rather than rent the place out (or sell it... some comps are sitting on the market for months and months, AND he feels that the market is likely to bounce back), he believes, and I think he is reasonable in his belief, that it is best for him to simply "bleed" the $2,000 per month cash flow loss covering the spread between current rent and mortgage/HOA + maintenance/CAPEX and wait for clarity to emerge. 

PITI $2473 no HOA?

What I’m getting at is could the homeowner (or another lien holder or even HOA) maintain the following?

Putting 25% down, with PITI (possibly an HOA) I would be at about $1800-$2000 a month. 

I am not familiar with the market but from what I have seen so farthere is an over saturation of condos and HOA fees are high.