Currently I own a large real estate company and still get some great value out being in his inner circle of real estate operators. 

Building real relationships with investors, brokers, and operators opened doors that wouldn’t have been accessible otherwise.

Massachusetts has a 5% state LT capital gains tax, but it generally follows the federal exemption rules.If the home was a rental property, the exclusion does not apply, and you may also owe depreciation recapture tax (typically taxed at 25% for federal).

So your super basic P&L may look like: $30,000 Rents-$3,000 insurance expense -$9,000 interest-$3,000 taxes-$8,000 operating expenses-$14,000 depreciation ----------------$7,000 loss on paper for the year  so negative taxable income But remember- $14k of that (depreciation) was something we didn't actually spend money on- so cash in bank at year end would be $7,000. 

Invested 3 years ago like others about $40,000 total which  included covering operational cost  for the first or so.  

@Ben CallahanRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Has anyone worked with them before and can shed a little more insight into how they work and operate? 

Typically a new roof only makes sense to protect the asset.

Landlords mistakenly ASSUME all PMCs offer the exact same services and operate the exact same way, so price is the only differentiator.So, the first question they usually ask a PMC is about fees - instead of asking about services.This also leads them to ASSUME simpler is better when it comes to management contracts.

What is the typical guest avatar in the area?