Hoping to house hack and use the savings to invest in another home. and rent that out to other potential students/health professionals in my network.

Being 1099 it can be difficult to find the right coverage. Why pay high premiums with high deductibles if there’s plans that reward you with full coverage of your healthy with ZERO deductible and low premium.

(whatever) I, too, was a multi family guy and the results on my health, pocketbook, and family were horrible. 

Since then I have had some health setbacks that kept me out of the game and set me back a little financially. 

You can possibly qualify for a partial exclusion if you had a valid unforeseen reason to sell after only 3 months, such as health, divorce or job change.

I ve seen many people loose health and even die from mold related issues. 

By blind luck, I began RE investing around 2008 when the village idiot could make money. 34 years of saving, lucky timing and military health insurance definitely helped. 

I sure have made some risky financial decisions like buying vintage cars to rent out to movies out of desperation but it was a smart move and has paid itself back in money as well as days towards my health insurance and pension (SAG-AFTRA) and will continue as long as they film movies in NYC at least.        

Hello,I have recently started shopping for lenders to have a cash out refinance for a second home in the Catskills.The home was bought roughly 10 years ago for $125k, we did about $60k worth of renovations and its current valuation is at least $250k.A family member with declining mental health owns the mortgage with $89k left to pay off at 5% and we would like to restructure so there are no financial ties left.Due to a spring fed water source, we have limited lender options.I spoke with a recommended local lender who claims due to us renting the home on AirBnB (we have a filed Schedule E for income on this property) it would only qualify for a commercial loan, subjecting us to a higher rate (5 - 5.75%) with variable rates after a set timeframe.Are we stuck with strictly commercial financing on this property? 

This needs to be mapped out before you leave the house, just like buying a property needs to be mapped out with relation to your goal before you buy.The challenge with asking multiple people What is your best strategy is unless they have a clear understanding of where you are going you will get completely different answers and none of them or all of them can be correct.Take the time to sharpen your mental axe before you take that swing, be as detailed as you can with end destination (What your life looks like in 30 years as a result of owning real estate) and then work it backwards.