As a fellow Northerner, I tend to buy in the Southern half of the US for 2 reasons:1) you get much higher year-round occupancy rates in the South & it’s simply tough to earn a good ROI in the North if your place sits vacant for a big chunk of the year2) Culturally, the Southern half of the US seems to be a lot more accepting of STRs regulation-wise.

Water is short-term issue, it won't be a material one.

I have a knack for saving on materials while providing some unique flair that will stand out in the market. 

Trusting lenders, agents, and contractors can be tough, but building a solid team and doing your due diligence will help ease that process.

However, it's definitely been tough to find solid deals that cash flow well as of late, at least on the long-term side I find it to be true, and counting on potential increased demand is a tough investing strategy. 

However, this is a difficult qualification to meet, especially if you have a full-time job outside of real estate.Don’t worry if you aren’t able to qualify for REPS status, because there is another strategy that is referred to as a “loophole”, which is the STR strategy.Per Section 1.469-1T(e)(3)(ii)(A): there are six exceptions where your rental property income is not automatically considered to be “rental activity” and thus may unlock the door for being able to offset these losses against your active income.The average customer use is seven days or less.The average customer use is 30 days or less and significant personal services were provided (for example, daily housekeeping).Extraordinary personal services are provided, regardless of the duration of customer use.The rental is incidental to a non-rental activity.The property is available during defined business hours for non-exclusive use by various customers.The property is used in an activity conducted by an S Corporation, partnership or joint venture in which the taxpayer holds an interest.If your property qualifies by meeting one of the exceptions above, the next step is to demonstrate material participation in the rental activity.

@Andrew Freed is a good person to get in touch with about that as he is a MA multifamily investor who does a lot of meetups.STR is a tough way to start right now because in most markets the table stakes to be competitive are very high.

the market is tough right now, with prices high, rates high, demand high, and inventory low. 

Buying a turnkey STR that will actually support the return needed for the time/money invested is very tough.

It’s always tough to hear when someone has a negative perception of our program and my knowledge.Addressing Your ConcernsSoftware and Support: Our Deal Driven software is designed to help our partners find and manage deals effectively.