REI investing for almost 20 years, owning a wealth management company for 22 years, suffice it to say there has been a lot go data/spreadsheeting/tax analysis/meeting with my team go into this overall decision to sell the entire portfolio at once.  

One of the biggest factors in successful flips is building a strong team: contractors, agents, lenders, and property managers. 

Looks like I need to talk to my accountant, but I was hoping to have this squared away before talking to him.I realize I also have this problem with my property manager.

I am planning to self manage as well and since there aren't many managers in my area I will likely employ a similar strategy once I decide to outsource the management.

On paper some of these buildings had amazing metrics, excellent cash on cash returns, cap rates, etc, but when I looked at the buildings I found the neighborhoods were rough, there was poor management in place, there was lots of deferred maintenance to address.

Investing in AZ, NV, ID, where you have family or friends that is a day away and you can start to build a network and team to help manage a property.  

Either way, clear communication with the guests about who’s managing the property is key to keeping reviews and satisfaction high.Permit Timing:The permit delay makes things tougher, but if you buy the furniture and keep future bookings, you might be able to use that time to update décor piece by piece without fully shutting down operations.

This is the foundation of why LaPlante Real Estate is based in portfolio management and property management... my personal portfolio started in 2009 and I find the majority tends to be Section 8. 

FCI, Provident, Madison Management, Allied are just a few.

What I can share is that the risk-reward will not be worth it as a 'newbie' due to your limited capital and inability to actively manage your properties.