I sent out my contractor to get everything he stated and much more fixed.Reached out to him again after his grievances had been met, now he's saying he would pay me weekly based on what he has and that he would pay the rest of the rent with this girlfriend's tax returns .So bear in mind that his lease expires in September, here are my thought: do i start eviction now, i dont think the courts are accepting eviction cases but i may be wrong, also there's also an eviction freeze in New York till July.Or wait till September to terminate the contract and go after him with the court.Thank You for your response

I recently stayed at a slightly different 1 bed property which is ~30 minutes from the area and closer to 'normal' civilization, Situation B, (with amazing views), and the owner said he has a 6 month peak of 100% occupancy and 50% occupancy the rest of the year.I've looked at AirDNA, which I've recently learned about, and the free views claim that that rentals in Situation A have 50%+ occupancy rate, resulting in nearly 2x the revenue I would expect from from the information from the management company in the area. 

There may very well be a decrease in demand for property in large metropolitan areas and possibly even some big changes in financing availability depending how the rest of this pandemic response goes.  

My further advice is to max out the Roth and put the rest towards your future RE endeavors. 

I would say maybe find a off market deal. see if the owner is down with " owner financing. use that 10-15k as a down payment the finance the rest of the balance through the owner ( be carful though, these are usually 4-5 years interest only payments) Then at the end of the term you will have a balloon payment for the remaining balance. with hopes of your property going up in value , through appreciation for remodel) then do a cash out  refi into a regular loan. take that money from the refi to pay off the owner. 

I don't care too much about the rest.

Also, some grading around the rest of the house to lead water away should be done as well.

If you put 10% down on a second home, you would have to show that you have at least 5% of the purchase price of your own funds and the rest can be a gift. 

I feel like we have a pretty good handle on what we are required to provide and feel comfortable saying no to the rest.  

If you're living in one, now you're out of pocket ~$800/month.How does the owner's asking price compare to the rest of the market?