We're both tired of the W2 grind. 

I've had smooth loans close with Kiavi and I've had rough ones, same with Roc.When Loans start to be troublesome:1) The borrowing entity docs are a mess2) The appraisal numbers are lower than expected3) Messy background reports4) Loans happening in an environment where market/rate fluctuating unpredictably 5) Your loan officer and their team are poor at their job6) Title issues that depend on county docs, that can be slow and painfulThere's more but it's Friday and I'm tired....

You buy it and now go to look at your beachfront and see a dumpsite of shingles or tires, that will cost you more than the lot is worth to clear out and maybe have the EPA just waiting for someone like you to jump on with fines for the cleanup. 

It's not to say I don't get sick and tired of stuff, but if it is worth it, I will continue to bang my head against the wall.

You reference taking out a HELOC and those are generally provided when the property is in your personal name, which I don't recommend for investment properties.Overall, it sounds as if you're tired of dealing with "long distance" ownership.

Years go by and eventually Grandpa gets tired of fixing porches, nailing gutters and steam cleaning carpets that 'have a couple more years in them. 

@Kenny Bao typically I’ve found my work in connecting in off market deals 100+ units has left me spinning my tires.  

I've been checking HOA CC&Rs to make sure they allow short term rentals.

Quote from @MIchael McCUe: Money isn't easy to save and $10,000( my debts) is a ton of money I want to save for a downpayment, I'm just starting so I don't have any money I would like to save $60,000 to buy a rental property, I think I could do it in  5-6 years, my brother filed bankruptcy and they relieved him of $6000 in debt from cash money.a list of my debtGst Hst Tax 4500 income tax from working with my dad I oweScotiabank credit card 1400Canadian Tire credit card 500cash money loan 2400Belair 600echelon 600should I pay the 10k back in the next while or should I file bankruptcy like my brother as It won't be for years until I am able to get a downpayment for a rental house anyway.Here are the negative consequences, in regard to real estate, of filing bankruptcy1.

Thus, they will contact every owner they can that has a rental being advertised, hoping the owner is tired and just wants to dump a headache of a property for 60-70% of market value.