And once the puppy starts teething, it will start chewing on things to stop the pain/itching, which can very likely be doors and trim

Employ a process for removing the outgoing tenant from the lease and charge a reasonable fee for this administrative work.

Letting that go will only cause more damage to your property every time it rains (wood rot, mold, damage to pain/walls, etc).The windows are a high priority item that you can wait and save up for, hopefully in less than a year.

So, I feel the pain. 

Renters are lazy, that's why they rent, help make it easy on them to stay.Fix all the issues she has in the 1st month, after that she should settle in and maybe bother you about 1 or 2 things in the next 18 months, if she is bothering you a lot more than that, either your place was a dump and you set yourself up for failure by not getting it properly rent ready, or she is a pain in the *** and it will never end and start making plans for a huge rent increase at the next lease or tell her you won't be renewing.

You already have some experience and with additional effort, will quickly climb the REI ladder to its pinnacle.To be more successful, you simply have to work on the other elements to progress your REI pursuit.As a fellow New Yorker, I share your pain with regard to prices and taxes.

I find its a pain to skip trace all of these letters.

Unlawful Detainer (aka eviction) is a pain, costs you both time and $$$.It's cheaper by far to just 'buy them out' and I mean offer cash for the keys.You need to decide what to do with any abandoned property and how to handle the deposit, but you're after possessing.

He would GC the project, and I would help on design, fixtures, and management/administrative items.  

It's been nothing short of a pain piecing that puzzle together to make sure I have no days of $550 / night rental open because someone didn't overlap a stay.That being said, I see how high rents have been getting around LA where I live and I am considering buying a property in an up and coming neighborhood like a Highland Park and renting it out for now and then maybe moving into it within 5 years.