Our homestead will likely include a main home, carriage house (guest house) with the possibility to build an additional guest houses as we hope to not only host our family and friends, but would also like to start a small bed and breakfast.What we bring to the table:- Real Estate Investing experience (I currently have 2 doors: 1 townhouse in Canada, 1 apartment in Italy)- Short-term property management experience (Canada/Italy)- Long-term property management experience (Canada)- Experience purchasing Italian real estate- Fluent in English/Italian (ability to translate)- Experience renovating using Italian building materials / systems- Trades: mechanical, welding (Him)- Successful entrepreneur.

They claimed on the disclosure that no violations of laws or regulations regarding the property, or litigation, and claimed no material alterations were made. 

@Ronald Allen Barney That is exactly why you do "alterations and repairs" no need for a GC as many are terrible business people.

This is especially the case if you are going to be on the hook for well over $100k.That is a life altering amount of debt.I know many people (mainly attorneys) whose lives are TOTALLY ruined due to the amount of student loan debt that they have. 

My point being if the advice on here is “Market data says…” you should translate that to what it means for your specific property.

Using a traditional mortgage, this translates to an out-of-pocket of about $12,500 ($10k down pmt, $2500 closing costs).  

If anyone can state what the question is, then they should also define the terms that are to be used so that people aren't constantly changing the terms to alter the debate.

Alterations that substantially improve the property to "like-new" condition may trigger reassessment.

There is absolutely zero tolerance for personal feelings/emotions in making business decisions which translates directly to also managing a business.

Here in stodgy New England local STR restrictions are spreading like a virus from town to town… just at the very point where the STR gold rush is already yesterday’s news and some investors are starting to realize that 2020-2021 were market anomalies created by a global pandemic that altered how and where people traveled/stayed.