Short term it is difficult to make the numbers work, the cost of new construction and the time it takes to zone-plan-build are usually the main reasons why private investors stay clear.

1.To extract equity in your property by re-mortgaging if you brought the property with a mortgage is normally not possible, it might be if you have extensive building improvements. 2.Getting a mortgage on a property you own 100% of is usually possible.

Most duplex properties are not in HOAs and usually in a renters street; lawns don't necessarily look great.  

We will both keep our W2 employment for the near future just looking into getting an extra income or make our retirement easier.

-Max LTARV is typically 75% -Is a 12-24 Month Interest-only loan with a balloon payment - Minimum credit score is typically 600 -Interest on the Rehab is usually paid per the total drawn amount. 

An LOI isn't usually a big deal and I've had properties ask to sign one before a viewing and there wasn't anything fishy going on with those.

It’s a bit intimidating since it’s outside my usual scope of business, but I’m committed to taking the time to learn how to be an effective landlord.

@Zach Howardyou can usually post enough information in a thread without the address and people will usually happily help you analyze deals. 

In MA, you can usually get insured with Fair Plan with certain pets, but it is VERY expensive.  

Charge extra for an ESA.