I was looking at an attractive rental but it looks like the land value is 75+% of the value, so I would be paying a ton get very little tax benefit. 

If someone doesn't pay their rent, then it can take over a year to evict them, and then I'd be left paying that mortgage and fees for a lawyer, etc.

Landlord will promptly respond to Tenant request for repairs but will not be monetarily responsible for tenant disruptions or inconveniences during habitable times of repairs or tenant/guest injuries incurred in or around obvious areas of maintenance, repairs, or construction.We are more converned about them expecting us to pay for their losses rather than getting recouped for damages to our property. 

Additionally, we have equity of approximately $145,000.Now, we are faced with a dilemma: should we sell our current property and purchase in a more favorable neighborhood, or should we rent the house and let it pay for itself.We would greatly appreciate any advice you may have.

I'm assuming I would have to pay it off if I won the house. 

OMG, please do  NOT take money out of your 401K to pay off a mortgage, especially not for a rental. 

am working with them now and had the first policy (with Spinnaker) cancelled for nonpayment/late payment so we rewrote another policy (with Millenial) and having the same payment problem again but at least they are communicating that cancellation is coming. they want me to pay by credit card over the phone so the payment wont be late and cancelled again. but when i go to mycoverageinfo.com to check on status it shows its been paid.

That being said, I'm always an advocate for paying for mentorship to fast track your goals. 

I have no problem paying a wholesale fee if there's plenty of margin for me. 

The seller's LLC pays capital gains tax and depreciation recapture, while the buyer's LLC uses the purchase price as the new cost basis.