Experienced flippers are more likely to understand the market, manage projects efficiently, and have a proven track record of profitability.

Speaking from personal experience my wife was not fully on board with house hacking and having a rental but she could see my passion for it all so she was kind of bought in. 2 years later she understands the concept and is fully on board with things. 

I do understand their reservations, but there has just got to be a way.Anyone have any input on this situation?

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.What else can we assist you with?

We grew up on the River and then Leonard Lake - I understand and agree about the winter - I live in Victoria BC right now, but have debated owning a lake front property in Muskoka - trouble is, with the changing Short Term rental situation, could be difficult to take on - I would love to go there in the summer for example. 

Your either going to beat your head on the wall because of the debt and stress about it making money or stress that you paid all or a substantial amount of your cash when you go all in. i understand this will be unpopular for a lot of BP viewpoints but it worked for us, we own 2 STR that we owe nothing on now and purchased both for 670k and have a real value of $1.2-1.3mm. it requires you to put a lot of your cash back to your reserves but you have it all to do it with.Personally we believe in ourselves and our ability to pick high producing properties(that is the very first and foremost consideration) then we went all in and never looked back, 2 years later bought our second STR with mostly cash. 

Within the city limits, I believe STR are prohibited, so start with understanding the regulatory environment. 

I understand their kids have special needs, but that isn't your responsibility.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.What else can we assist you with?

Prorated taxes (I understand this part)what other items that i should see on my closing bill?