Landlord may place signage on the Premises or show the Premises to perspective renters or buyers during the last thirty (30) days of occupancy or any time the property is listed for sale.When she failed to let the contractor in the second time, I texted her to let her know that we would schedule a third attempt.

Should I attempt to get my $500 back and if so what would be the suggested way of going about it or just let it go and lick my wounds?

You should attempt to estimate the average to remain competitive, and then any overages could be factored into rent or surcharge increases the following year, assuming you were not extremely far off in your estimates.

The "president" keeps ignoring my emails and attempts to discuss problems, so I'm at the point of getting legal representation.

Did my first analysis with an attempt at inputting actual expenses versus using 50% rule.

This is by no means an attempt to push anyone into any market, but rather just some generally vague thoughts. 

In Massachusetts they just enacted that we can not file any evictions till 45 days after the emergency is lifted.

Building on the eviction moratorium put in place by the CARES Act, the new relief proposal would enact a year-long ban on eviction filings over nonpayment of rent for all residential tenants, a bold and unprecedented move for the US.

I am attempting to take the plunge into investing in real estate.

I'd be cautious about doing a cash out refinance too close to the sale or purchase because under audit, the auditor could possibly view it as attempting to avoid taking cash at closing because that is taxable.