I’m in the same boat.  16 years producing some of the largest concerts on the planet and managing clubs and theaters across the country.  

So we (my wife and I) have made a concerted effort over the past 6 months or so to invest outside our small, rural local market in Charlotte, NC - a very competitive market with low supply/high demand.

I can't wait for all the sports events, concerts, and conventions to start back up. 

And the loss of amenities like concerts and shows also made urban apartment living less attractive.Congress granted mortgage borrowers struggling to make the monthly payment forbearance, reducing the pressure on them to sell and keeping a source of supply off the market.

If your vacation home happens to be located near a major event — like a PGA golf tournament or a big multi-day concert — you may be able to rent the place out for a short period even at high rates and pay zero federal income tax.Tax-smart year-end strategy: The more rental days between now and year-end, the better — as long as they don’t exceed 14 days for the year.Rented more than 14 days with substantial personal useYour vacation home falls into this category if you rent it for more than 14 days during the year and your personal use exceeds the greater of:(1) 14 days or (2) 10% of the rental days.

My experience comes from throwing concerts and nightlife for the past 5 years and brokering residential mortgages since 2005.

Since you are just starting out and have a FT job, I would say work with an agent to start and then if your volume of flips, buy and holds, or if you concert to investing full time, then you should consider getting your license. 

I'm assuming 4% a year apprechiation for my area, but with this giant casino going up next door (only one in Boston area, concert venue as well, etc.)

That way, you represent one potential vote, and you will carry weight.However, it is still ridiculous to think that a man who became incredibly wealthy with real estate investments and understands what a critical role they play in the U.S. economy, and who used Section 1031 in every single one of his deals, will now make a concerted effort to do away with Section 1031.This "article" is still a blatant attack on Republican values and based on something they haven't even done.  

Probably some concerts and similar type of events.