The buyer is also asking me to declare the sale at around 90k, which is certainly a red flag, so wondering if thats something to avoid altogether.

I love the Worcester market, but wow it is red hot right now.

You'll end up paying $127+4k for a house that the market has demonstrated is only worth $130k and you will have done so with someone against you, not in your corner, rooting for their $4k fee regardless of the fact you're making an investment that the market testifies is backwards. 

A lot about them sent up multiple red flags.

That is like walking up to a roulette wheel that has hit red five times in a row and saying that means the next spin is black.

I like to roll it all up into a spreadsheet documenting the date of the last update, performance and then I give it a green, yellow, red indicator that correlates with all good/ no problems, monitor, intervene / liquidate if applicable.

For example, my lease says (in part): "Tenant shall be charged for repair of drain blockages or stoppages, unless caused by defective plumbing parts or tree roots invading sewer lines."

Living in Oregon wine country requires a lot more cash than my farmboy roots in Michigan.

I'm sorry, Jon, but it sounds an awful lot like you're asking us how to draw seven red lines, all of them strictly perpendicular, some with green ink, some with transparent ink.To clarify, not the task, but the general sense of how this is being asked, do you want to retain the right to get rid of the tenant in the winter months for nonpayment of rent, egregious lease violations, your decision not to renew, etc.?

Economists and real estate agents say the housing market has been red hot because of the COVID-19 pandemic.