The cost of the program is 35K upfront and then approximately $3500/mo for all marketing.

You can always consider doing a cost seg study on a property that you buy and that can also help with tax benefits if you cannot qualify for the real estate professional status.

What are the pros and cons of each, and which offers the least restrictions, flexibility and cost savings for my intended purposes?

Many months of costly vacancy, local market rent & resale deteriation, special assessments, property taxes and maintanance fees suggest a quick sale would have been the wise thing to do 2 years ago.

It’s inexpensive to provide but can make a big impact.Comfortable Bedding: Investing in high-quality mattresses, pillows, and linens improves the guest experience and leads to better reviews, which can boost occupancy rates.Smart TV or Streaming Services: Offering Netflix, Hulu, or similar services is a low-cost way to enhance guest entertainment and stay competitive.Fully Stocked Kitchen: A well-equipped kitchen with basic appliances and utensils appeals to families and long-term guests, saving them money on dining out.Dedicated Workspace: If your property caters to remote workers, adding a small desk and ergonomic chair can set your listing apart.Outdoor Spaces: If your property allows, an outdoor seating area, fire pit, or hot tub can significantly increase your nightly rate and attract more bookings.Energy-Efficient Features: Guests appreciate eco-friendly options like LED lighting, smart thermostats, or solar panels, especially in eco-conscious markets.Keyless Entry: A smart lock is a relatively small investment but offers convenience and security, which many guests value.If you’re deciding on amenities to add, it’s always a good idea to research your local market.

I am estimating the note would cost 2.5k per month at most. 

Even if I were found guilty, the cost would be in the thousands, not in the millions.

I want to know is it more cost effective or easier to purchase the property alone and put it in a mortgage in our name or purchase the LLC from him that holds the property within it.

Insurance is still an annual dog fight via my broker.Read your policy very carefully, consider replacement costs will probably be higher than estimatesResiliency is a requirement here.As far as sell or not....it'll depend on your determination to be here.This ain't the burbs of the bay area.Prepping for heavy rain right now.

We're looking to gather info about likely cost, pitfalls, time required, considerations when obtaining financing, etc.