Additionally, I’m up for long distance investments but I would definitely need some mentoring there because it was hard enough managing the VT reno from Boston.My current strategy would be to rehab/flip a few houses a year so I can leave my W2 job and also add some buy and hold rentals (MFH, STR).

You need to hold your own against the competition at a bare minimum and better yet, stand out.

My Buy and Hold portfolio is still cash-flowing with rising rents in Chicago Suburbs.The In-migration and flight from certain markets may continue.

Are you looking for something that is rent-ready now, or something where you can force appreciation and look at a cashout to be able to rinse and repeat?

(Obviously your primary would not be eligible for a 1031 but would be 100% tax free.) if you owned it less than a year you’d owe regular taxes and I’d suggest holding on for a year if possible. 

Fix and flip, wholesale, buy and hold?

Would this be something that is covered under the umbrella. in both of these cases, would these be something that my umbrella would cover, paying for an attorney to fight the termination and also paying what would not be covered if the company holding the regular policy will not cover the damages, even though the regular policy has sufficient coverage i.e. the limits that are stated in the policy should far and above cover what is being asked for repair.

@Megan Elliott, There's no statutory holding period. 

If the answer is yes then sell it, if the answer is not sure or no, then I would hold on to it. 

Set some clear goals and hold them to it.