I did one in Philly and Never again way too many rules and time to get them through..

Irina, there’s a lot to unfold here. if you are looking for the rental cash flow to assist in covering the cost of living in Florida, maybe the best option is to sell your property in PA and use that money to buy a multi unit in Florida this way you accomplish both option.

Sometimes the homes we buy to live in don't become the best rentals and your money can be used better on a different asset, especially in Denver. 

As soon as you get an offer or 10 minutes before the buyer’s agent shows the property?

What's your best piece of advice or tip when starting out managing a STR?

As mentioned residency 2:5 goes a long way in helping assuming 250/500 or less Btw the 500 consult fee you would pay a CPA is work every penny.  

When we purchase our upleg, how can we best negotiate to protect ourselves?

Per my door contractor Home Depot and Lowe's have the best pricing on entry doors because of the sheer volume they do each year.

Primary you can go as high as 90% CLTV and investment 80% Max LTV but with most DSCR or lenders 75% MAX investment.Best way to map this out or to make sure your taking the right steps with the right property is to have a long conversation with a Seasoned Banker and your realtor. 

Cap Rate: Provides a quick way to gauge an investment’s return based on the property’s income relative to its price or value.