If just going this path is more practical it would simplify things significantly, but everything I understand says introducing these new activities and the respective liability could expose our other property to risk if a nuclear claim occurred related to either property if they were part of the same LLC. 

He now sees he has to walk before he can run and there's absolutely no reason at all to look to expose yourself financially to the max right out of the gate. 

Are they doing everything possible to expose properties to the broadest possible market?

Broadway or crypto has a shorter run than 7 years, you exposed yourself unnecessarily.  

@Jonathan Heacock if you go with a wholesaler, understand that they will only expose your property to whoever they have on their distribution list.So, recommend only giving them max of 30 days to sell it.

My second slow season I decided not to rent it out because the propane bill to heat the home wasn’t worth the hassle, this last slow season was record snow and many homes lost power and heat for several days, it was categorized as a natural disaster.

At that point, your ENTIRE ESTATE  is exposed and subject to discovery in subsequent litigation.I am not an attorney and this is not legal advice.My $0.02 ...

If the policy lapses or is canceled due to ownership changes, the property could be left uninsured, exposing both parties to risks.

My concern is exposing my anonymity and other property attached to my LLC since there will  be a correlation with my name to LLC on sale history record?  

Also, improves your position in pricing should rent prices turn bearish unexpectedly during your vacancy time so you can be flexible in pricing in negative economic environments.Con's are more on the side of the whole concept of using the long term locked-in period with the bank essentially utilize inflation to 'short the dollar', as well as the more rapid diminishment of the mortgage interest paid tax advantage.All in all it is safer in a lot of respects to get to that property free and clear, but the major downside is missing out on the additional value that is derived from the power and monetary benefits that come from having a healthy expose to mortgage and other forms of financial leverage.