So I've been looking to purchase a rental since the beginning of this year, but I've run into a couple obstacles.

I am a RE Broker and have been one for 50 years now.. but I have not sold RE at the street level in about 15 years or so other than referral fees. here is my point of view.Listings will be worth more than they ever have been in the past I think thats self evident.As a high volume Seller of property here is how I am going to work it..

Live several months a year? 

Was able to get an offer from a broker for a fixed rate HELOC at 8.4% for 120k over 20 years.

Literally maybe 3 month old article and really contradicts a lot of what you said:https://www.benoitproperties.com/news/miami-housing-market-s...

I have a side by side duplex I have been house hacking for the last 4 years and I am unsure if I should keep it or sell it.

Croix for 18 years and still work as a virtual legal assistant for several attorneys on St.

We use a YTDpaystub and last year’s W-2(s) to calculate income several different ways:Hourly or salary income calculated to a monthly amountYTD income divided by number of YTD monthsYTD + W-2(s) income divided by the corresponding number of monthsIf these numbers vary too much, then we investigate and require an acceptable Letter of Explanation.Employment StabilityUnless an applicant has exceptional credit, we strive to determine their stability of employment to make surethey’ll always be able to pay the rent on time.

Basically ~50 years including my mom’s rental without an eviction.   

Since the same reporting period last year, asking rents have climbed by 0.8%, up from $41.89.