Any contractor can work on any rehab project but just because they "can" doesn't mean they have the knowledge or understanding of the unique nature and intricacies of the rehab loan guidelines, paperwork, timelines, compensation structure, etc. 

Fast forward to present time and my mom has offered to sell the home to me for $100K (currently appraising @ $200K) in which she would repay my grandmother and pocket $50K.

I’m an inexperienced real estate investor living in Texas, and I’ve come across an opportunity for a very unique home in Jersey City, that I think could be a good short term vacation rental.

If you can be of any help or interested in getting an extra hand free of charge other than just repaying me in some mentor ship for my labor I would love for you to shoot me a personal message.

With that being said, the current Covid-19 environment is very challenging for landlords trying to rent a vacant property while trying also to keep you and your family safe and healthy.Rent-o-meter as @Marshall M. suggested is a great tool for normal property types, but given the uniqueness of your property I would also recommend tapping into a locally established Property Management company in Napa that can give you more insight into 1) current demand given Covid-19, 2) historical demand for a generational living setup as you currently have and 3) expected rental income for the setup you have and the given amenities.As an owner and investor, there's no reason why you cannot continue to keep the property listed to catch the right buyer for your property, while at the same time placing it on the market to see if you can get a Tenant in at a price point you are comfortable with. 

Sarasota is truly a unique animal all to itself. 

And because he just doesn't do a lot of business, that means he's not up to speed on the latest changes in guidelines, process, etc.... if you're a cobbler with some unique cobbler quirks and mortgage implications, he doesn't know what those are, since it's been 5 years since he did a loan for a cobbler. 

This is due to the very unique combination of economic factors at play here, namely housing shortage. 

It also has a lot of bars, restaurants and other things that draw crowds to the city.The $6.0 million USD restoration project was done by the building's owner, the Great Lakes Center Foundation.Reaching out to them for more guidance (and strategy, as well as potential pit falls) on this might be beneficial.And calling the general contractor (ask the owner who it was) to discuss any unique problems they faced on this restoration might also be intelligent.If you ask (offer to pay) they might also be able to provide you with preliminary guidance on construction budgets as well as contractors lists, and vendors lists (if you think having them would help your efforts, feasibility, etc...).Another phone call might be to the Architect to get his thoughts on this.Contacting these people would be beneficial because they have successful experience on doing what you want to do in a similar sized city, within driving distance of Ontario. 1)  http://bay-journal.com/sfp/pmrr/index.html2)  http://bay-journal.com/sfp/pmrr/pictorial.html3)  https://www.gogreat.com/cities/bay-city/events/4)  http://www.bayfoundation.org/who-we-are/pere-marquette-depot5) This should bring up articles about the Train station Restoration from the Michigan Newspaper (mlive.com): https://www.google.com/search?

There are no hotels in Pilsen and I think that they have a unique product they are offering.