The mountain house has taken almost 2 years of breaking even and using some of the income on improvements until we have been able to cash flow.

What starts out as a delta ( wrapping the underlying and taking in the difference) started to break down ..

Quote from @Marc Winter: This is rapidly becoming the 4th boom/bust cycle I've seen.  

Thankfully I am currently breaking even on the mortgage with both units rented and we just moved into my girlfriend's parents’ lake house rent free.

There is a lot of new things about to break ground.

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

You are telling the tenant in advance that they can break their lease at any time and get paid to do it.

But if you are saying that is always breaking or giving you issues, I know that can be a make or break.

The operations will make or break you. 

We are also temporary heat providers for most large construction projects in and around Buffalo NY, neither I nor anyone in the industry that I know if has been contacted about setting up temporary heat for this project which is normally one of the first steps before a project gets into winter. thats a nice cottage industry winter heat..