And with an HOA handling maintenance, have you checked their reserves?

Check their occupancy, nightly rate and amenities.

If you are just starting out, this is for you:When you buy an investment property, it is treated differently than a house you are going to live in. 

I can check in with my local bank, but I don't want to waste their time when I'm not yet serious about doing a loan with them.   

If they are professional, they can explain this quickly and easily.

Had a quick question.I purchased the property for $500K about 10 years agoI'm selling the property for $575K with the Fire DamageI received an insurance check of $380K for the fire damage.After Paying off the Mortgage + Escrow + Realtor Fee's, I'll be left with about $150K.My question is will I get taxed on this $150K?

In order to do so, I would need to do a cash out refinance of the first property, and was told I can pull out $80,000.

I am not sure, but I imagine that you could also help out and lend your credit to this type of purchase. 

Most agency loans will expressly forbid such an arrangement, so if they found out, the odds of having the loan called would be very high. 

He's an educator and does make money selling education, but like most of the others doing this, he began by doing deals.