@Natan Gutt, I am not understanding why you would need, or even want the full value of the voucher.  

Fortunately, all three inspectors (from different departments) were very supportive and one inspector even stated they will not return, even if another complaint is filed.I want to offer a cash-for-keys option, but since the tenant's attorney is from a nonprofit, I feel she will fight for her tenant to stay.

I'm looking to purchase my first short term rental in an expensive market and was wondering about how many people are able to manage their own properties even potentially clean, fix them.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

Also, they don't have a search filter specific to LTV, owner equity, etc...Any suggestions on any other software that could assist with this pretty specific search?

There are over 20+ active CPAs here in Biggerpockets assisting RE investors with their tax planning.

Even if the ADU adds value close to the cost of adding the ADU, there are other reasons that adding an ADU is often worse than other RE investment option. 

It's changing the whole vibe of the city.Worcester used to have its own identity, but now it's become a commuter hub for folks working in Marlboro/Hudson, Natick/Framingham, and even Boston, thanks to remote work options.Let's break it down.

A knowledgeable realtor should be comfortable discussing these concepts and applying them to potential properties.Ask about their network of contractors, property managers, lenders, and other professionals who can assist with your investment.Taking the time to find a REALTOR with the right experience and expertise will help ensure that you make informed and profitable investment decisions.

Prices have gone through the roof in Ludlow in the last year to the point where most of my analysis only breaks even if I am being conservative.