I don't know if the current insurance company (loggerhead) where I have the open claims is willing to renew the policy or not.

Buyers have trouble underwriting deal with current rates, so price goes down.  

Even if you are a US Citizen and live abroad you may run into issues as you are not currently living/working in the US. 

Many people juggle lines of credit to meet current obligations.

Currently one property ready to go and I want to do 30 day plus rental and back fill open days with short term.

That’s great advice Taz, I’m currently working on saving enough money to get started, house hacking is hard for me at the moment because I just bought a house 2 years ago, I would have to sell my house(which is in a great neighborhood great location) and use that money to fund the duplex which isn’t totally out of the question, I would like to keep the house if possible but also would like to get real estate investing more.

My name is Wes and I live about an hour north of Toronto, Ontario, Canada.Looking to get into real-estate investing with long term rentals, BRRR, and House hacking.Currently looking to also find other other local people to chat to about real-estate and how to get started in our currently price inflated Ontario market.Let me know if you're in my area!!

Quote from @Gabriel Williams: Been listening to BP for several years and I’m currently working on our 5th deal.

Do we focus on flipping, (currently we have actually been trying to do this, but we physically can't find enough contractors in our smaller market <100K population to do that much work).

One thing I wouldn't do is jump into "giving it a try" without the eyes-on advice of a current self-managing owner.