You can do this with a few different contractors for each trade.

Check with your insurance company first - they might have an opinion on what you are planning on doing

For these types of questions - it would make sense to start by getting some quotes and term sheets from actual hard money lenders (larger companies, found via google or the directory on BP) - can still do the private money - but these terms they give you can easily be the starting point - and you will likely get a lender to walk you through them for free anyway

I don't want to ask the insurance company first incase it flags something wrong.

No big, national, publicly traded banks will do this loan type.

Purchase price: $68,000 Cash invested: $5,000 Sale price: $99,000 4 Unit quad in Medina NYRenters were tough and management company's locations are too far for a regular check up.Had a renter pass away and then DCS came in and the house was condemned due to farm animals in the upstairs unit where the person passed.We were too far to keep tabs on this investment so we sold the home.

My company is a sponsor at the GOREIA, so we are there every month and I also go to smaller ones in the area monthly. 

Note to self - always go with a larger company who will be around for the long haul.

I gave the tenants the option to either maintain the lawn themselves or to have my lawn company maintain it at an additional cost in their rent.

You can also run your STR in your personal name or elect to start a company that operates the STR i.e. branding.If you do not qualify or for some other reason do not want or cannot qualify for conventional financing, you will likely have to go to some sort of DSCR or other business purpose loan route, and they will actually require you to put it into an LLC.