In your case of a fourplex, option 2 should get you a better deal.I would also agree with Bill on how the number of units may not correlate with the value of the property unless it is a large multifamily complex, and sometimes a fourplex or several single family houses would give you better returns. 100% We always recommend conventional first until you can no longer qualify for those. 

These special assessment were thousands of dollars, and there was no sufficient reserves from the monthly fees to cover these large biggers, so the owner were required to cover the shortfalls out of pocket, what a great way to ruin your cash flow and ROI.There are benifits to condos, including tennis courts, playground, swimming pools, club houses, and fitness facilities. 

I have used avail.co in the past with great success but it appears this software and others no longer market on zillow which I know to provide a lot of leads in the past. 

It's no guarantee but it's a good place to start.

Yes or no" and I marked yes and added dog. 

Visiting parents and college sports fans are coming to town no matter what, so the key is making your STR feel like the obvious, no-brainer choice.

No reason it should cost that much otherwise.

Current tenants have no motivation to show the property, or to make sure that it’s clean and ready to be shown.

I guess I’ll have no choice but to use dscr 

If there is little or no appreciation, every investment dollar must come from your savings.