I have a scenario where there is an overlap with (current) outgoing tenant move-out and incoming tenant move-in dates during the middle of Jan 2022. 

@Dave Spooner Absolutely, the potential of decreased turnover from having a more desirable up to date property can also have a large impact on consistent cash flow!

Depending on the state laws, your tenant may not be able to get rid of his guest at a later date without going through an eviction -- would be good if he knows that ahead of time and has the tools available (ie guest being a subtenant, not a "regular" tenant). 

You may be able to get a non-refundable option payment from the tenant-buyer and can potentially contractually lock-in a premium above the market value on the future sale, which may prevent you from losing money on the resale, if the buyer can actually complete the transaction at a future date.

There is no reason to get married without dating first. 

It can be exhausting trying to get this information yourself via the internet when so many "sources of information" offer conflicting reports or just blatantly try to push you through some sales funnel without bothering (or caring) to address your actual concerns. 

My county has very up to date aerial images.

We also included a "To Do" section of smaller things that we had to take care of with dates to complete them.Does anyone have any advice on tweaks I could make to the one that I created??

The way the the 2nd home rider (the rule) is written is something such as "The borrower agrees to keep this home available as a 2nd home for the borrower and to not place LTR or professional property management for 1 year AFTER THE DATE of this executed second home rider".

More details will be released closer to the date at which the product is released in March.