In addition if you use a title company or lawyer to handle the closing then they are legally required to report the sale to the IRS etc.

So, how you want to handle that is sort of up to you.  

Otherwise many many many agents spend a lot of time and effort finding property and writing contracts only to find that the funds can't be transferred, or they don't have immediate access to the funds, or they need some kind of approval from 3-4-5th parties, or there are exchange restrictions, or 9000 other excuses.You probably need to find them a commercial broker who can handle whatever kind of investment they want to make. 

This is how the majority of investor are handling rehab projects.

On the other hand, I could hold on to the property with the thought that I can handle the expenses of keeping it, while continuing to pay off considerable equity and gaining appreciation for each year I hold on to the property.I would love to hear everyone's thoughts on what is the best option, as I have been having trouble making a decision given my limited knowledge and experience. 

How are others handling this?

Many banks handling tax escrow accounts for mortgages have mistakenly thought there was one tax due twice/year or totally missed one of the taxes.Investors should research the SEV and the Non-Homestead property tax millage rates to project what the property taxes will be after adjustment.

Determine how much money would be needed to handle each risk, and determine if you have sufficient liquidity / cash flow to ensure you can “stay in the game”.This is of course in addition to all normal “due diligence”, financial forecasting, etc. 

But other than telling a prospective tenant that "this is not the house for you if you have a problem with the security cameras", how have you handled the situation when they bring it up in regards to it being an "invasion of privacy"?

How do you handle contractor schedules and supply chain slowdowns?