What we find is that owners in your position can do well in a set of ideal circumstances:  the home is in great condition, they find excellent tenants who treat the property with care, and nothing crazy happens. 

Unfortunately, factors beyond our control often dictate these decisions.

However, if circumstances do indeed change over the course of the loan, there shouldn't be a penalty involved if you move into the property down the line for unforseen / unintended reasons (such as maybe in a couple of years there is a family emergency requiring a need to temporarily move into one of your rental properties etc)

If this is an insurance claim the process is very different than hiring a roofer during normal circumstances.  

Every circumstance is unique.

IMHO none are "hand holding" you need to unfortunately spend a lot of time figuring out how to get each tool to work.If you have questions, their process is that you create a trouble ticket.   

Unfortunately I should have asked for advice before I started the process with the current tenants.

Will absolutely push the due diligence time in order to make the decision and if the seller is unwilling given the circumstances, i think as you implied that is perhaps a bigger red flag than anything!

Depending on the facts and circumstances of the agreement, it could either be treated either1) the sale occurs as of the original agreement date, and then your taxable gain is generally spread out over the life of the principal payments as an installment sale (although I should mention any depreciation you've taken on your property could affect this), or2) the sale does not occur until the lease option is exercised, and gain reported at that time.

Tough time to sell a condo as inventory is crazy high and unfortunately, going to get higher as they keep building.