Are the units you own in NY? 

Hopefully your Realtor is experienced in listing/marketing STR properties and understands the values of a fully furnished unit.The resale market is full of STR units, so it could take months to sell.

After that, you rent out the unit you were living in and get more cash flow.Alternatively, you can partner up with someone with 20k also, and do an investment for a rental.

Personally I think I don't want to deal with pets because a) it's a condo complex and I would feel bad for the neighbors if a dog was sitting in the unit barking all day while the family was at the beach, and b)  I live 900 miles away and would not be available to assess any potential damages incurred by someone's pet.  

Yes sir market rent difference is 50-100$ per spot per unit (so i 1 car is 50 less than a 2 can and no garage is 100 less per side.

Assuming you're living in a unit a new build as a rental can be challenging from a numbers prospective.

I own a rental property with great cash flow.  3 1br/1ba units and a 2br/2ba unit.  

I’ve looked into OOS markets and can’t seem to find those golden deals others talk about that are priced under $200K for a 4 unit and cash flowing $700/unit.

Investment Info:Small multi-family (2-4 units) buy & hold investment.

Ask them how many units they manage, what they feel market rent for your property is, do the handle repairs in house or use contractors, what mark-up do they charge on repairs, etc.