In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

When I purchased my first property in 2020, I feared then that COVID would cause a downturn, but I was thinking longterm and got "lucky"Many experienced investors I speak to have the same few regrets 1) I wish I started sooner2) I wish I bought more3) I wish I never sold

I am not very concerned with cash flow and am looking more towards appreciation and equity. 

My concern is more in the legalese of the deal.

This reminds me of a police officer  pulling somebody over without reasonable cause and asking to search their vehicle and if the person does not consent, they’re saying you must have something to hide.

It's not enough money to be concerning yourself with better ways to re-invest the funds.

Appraiser's learned a valuable lesson in 2008 when they were accused of being one of the causes of the great recession.

If you ever want to have a discussion to explore your options or ask any questions about the concerns you mentioned, I would be happy to help! 

Working with a 1031 exchange specialist can also help keep things on track.Bottom line: Start early, have backup options, and consider a reverse exchange if timing is a concern.

I would limit the open calendar days on VRBO to maybe only 30 or so out so as to not cause any/many issues (having too many dates show as booked) when I subsequently go live on Airbnb.