One red flag to me was that he didn't really want to pull permits for the work.

Plans/permits/rehab was about 7.5 months.  

Still does nothing to address to significant lags in viewing my AirBnB inbox on the web, but since State of NH is still not permitting STR bookings even after their lodging task force recommended they open today, it's all a fairly moot point anyway. 

Can anyone please let me know what would be a good way to get/make basement drawings to submit to city for permit ?  

I'm a developer - buy, entitle, permit, finance, build, operate larger projects - but regularly have to deal with the same thing you're asking about - how can I fairly compensate someone for their contribution to a project? 

I paid for drawings, survey and waited two months as  I applied for permits, only to find out that two units on my parcel would be over the limit per acreage.  

Also permitting would pretty much force your hand.

We did a lot of the work ourselves but it still cost about 30k since we hired professionals for permit work and replaced appliances.

So, I would treat the deal as if the seller is striving in every way possible to rip me off, and I would verify EVERYTHING; I would go to city and check on all building permits vs what there, rental licensing, zoning, I mean literally everything I would leave nothing to chance what so ever. 

Due to permit issues if you can believe that it’s been a year.