I feel pulled in both directions - go all in on a good deal or be smart and wait for the next one because I am pretty leveraged (and tired) as it is?

He had become tired of the upkeep and work involved.

i dont feel tired at all!

Many sellers are tired of being landlords but wouldn't mind collecting a check every month still. 

They are like tires on an auto in this way, people think there forever but I assure you they wear out.

I was the only serious tire-kicker on the deal across an 18 month period.

I am sceptical seeing more and more insurance companies pulling out of FL, leaving a state sponsored program the only affordable option - until the tax payers are tired of funding it.   

We were tired of moving so I wanted to purchase a property directly as a rental instead of living in it first.

Disclaimer - I am not an CPA or attorney but I became financially free doing this for myself after 10 years working as a w2 engineer :( and I am sick and tired of seeing highly educated and hard working professionals getting stuck in the rat race because we deserve financial freedom and the option to do more with it.If you are able to implement a real estate professional status tax strategy (REP) you can use passive losses from syndication deals to lower your ordinary W2 income.

I'd even recommend looking up on public records of some beat up small family in the area and calling them personally to see if they would sell you their property that needs work, especially if they owned it over 10 year, that usually means they are tired of it, and investing in bigger projects.