If you can figure out the thought process and principals that experienced operators have, then you will have a better opportunity to invest and dispose at all times in a cycle.

And, yes, join a local real estate group because the principals of investing are the same - just the markets are different. 

Some cost are simply necessary business expences for landords with principals. 

My goal for these transactions, though, is to hopefully be win-win in that the person or entity giving me the money benefits from our deal just as much as I'm benefiting.The easiest example might be this: I still have a day job as a principal software developer where my employer pays me a LOT of money.

@Xu Som Got it...it's probably wise to get a good read on the value of your property to determine what your equity position is...most HELOC's will go to 90%+ loan-to value...It really just depends on what you're after...if you just need the down payment for a new property, the HELOC is a good option...but you'll have an additional payment to cover the outstanding principal on the HELOC...so renting the primary for additional income is a good plan if you can swing it.There is a delicate balance here in not becoming over-leveraged....you'll have 3 mortgages in the end...

(AA) "Associate broker" means an individual licensed as a real estate broker under this chapter who does not function as the principal broker or a management level licensee.

I rent it seasonally and pull in around $20-22k a yearDoes it make sense to stay in this when my rental is only paying 50% of my expensesI know that I'm paying down the principal and my thinking was to hold on as long as I can because of the Naples market.

@Darren Campbell @Jeff Moore - do both - accelerate the payments and save too.The loans are interest heavy in the begining portion - pay them down accelerated till the principal payment becomes the majority percentage in the payment (and it's up to you where that point is, personally, I would look for 75%+) and then let them ride since the rates are low and you are unlikely to get that low rate from anywhere now.

Tenants will be paying the bulk of your mortgage payments, you'll build equity via principal paydown and appreciation, more tax benefits of owning vs renting, and you'll be living very subsidized and able to save that much more cash to roll into your next investment property.My advice would be to zero in on what area you'd like to live.

I would note that with properties, you can also get more return from appreciation of the property and repayment of your mortgage principal as well, so you'd need to target more than 12% for your project (since you will not get returns from those two).