We wouldn't even offer to clean this up as lawn maintenance is 100% on tenant unless an act of nature causes damage.Review your lease and make sure this is covered for future unrealistic tenants!

But if you are using seller financing and a regular CRE loan, the seller will need to be comfortable subordinating.

If you are local check up on your contractor regularly. 

Most investors I work with do either a regular refi DSCR loan or, take up to 75% or 80% of equity out of the home through a cash-out refi. 

I would start off by getting several quotes.I can tell you that my regular AC guy charges 40% more than the guy I go with.  

It looks like your seller wants to seller finance the deal to 'be the bank' - which can be great - maybe you can negotiate a better deal on interest rates than what is currently going on in the regular market - which would be awesome.As for which home first - I would definitely go for the duplex you are already in.  

I invest regularly in Worcester, Providence, and towns outside of Worcester. 

Banks do this regularly during any kind of financial hiccup.  

Otherwise it is nature and misquotoes , ticks, bees and spiders live outside. 

That will help keep thing square with the guests.Remember that you need to do a full background check etc etc with a regular full lease for the time they are there.