also, they can list the property in different platforms for a small fee!

Waivo has a different but similar product they sell directly for STR.

I have researched the different kinds of loans for this but I would love to speak with any lenders or other investors in this area. 

I see HELOCs as low as 7.5%, so the difference is not that significant.

If meaningful appreciation is on the horizon, its a different story.If you were to go the financing route, blanket loan may be your best bet through small local bank or alternative lender.

How long it takes to be financially ready is different for everyone.

Since you're in Texas, I'll use a town like:  Each town will be different based on the population living outside of town. 

I would highly recommend Realty One, the realtor Derek helped me solve all the major issues that came up and supported me in running the numbers for different properties.

Lenders can have different loan options based on the property type and the amount of rehab (if any) required for the project. 

build a multifamily property and continue that strategy. building is a different strategy that allows you to still enter hte market below value. this is what we build in columbus ohio for investors it's a 3 story walk up infill that's about 24x40 and 2 bedrooms 1 bath stacked 3 times. it's identical to like 65% of apartments that are built. you'd need probably 100-150k in proceeds.