We have occasionally run into issues with the Internet being down at the STR and it not all going through with a tenant now using a code that doesn't work.

Has anyone found lenders (preferably credit unions or small local banks) that do HELOCs on investment properties, or are okay with a tax return that shows income generated occasionally on a 2nd home?

They have study guides, practice exams, flash cards, and much more.

Our expenses are about $1,400 monthly (plus the occasional oil fill up).

*Open the windows, use the vents, and air the Premises out occasionally as needed. 

Occasionally, I'm asked about two or more people pooling their resources to buy properties.

Flash forward 5-7 years - Most likely you will be cash flowing and debt was paid by resident and you will also have a loss to carry over on your w2 income.

. $100k doesn't go far out here but there are still deals to be had. 2 family, full rehabs in the lower to mid $100k range come my way occasionally. 

Yes I mean that in the past we occasionally took 2% *didn't like it but let it slide and now that the buyer broker sets minimum percent we are now at 2.5% firm minimum which is an interesting turn of events. 

Taxes can vary significantly by location, so this is an important factor to consider.Maintenance and Repairs: Plan for ongoing maintenance costs such as landscaping, cleaning services (if not done by yourself), and occasional repairs.