Pardon my tax ignorance but are the benefits of doing so really that significant?

For example, someone calls in and you chat with them to find that they may not be interested in selling right then at your price for whatever reason, however over the next several months their motivation may change so a follow-up system should most certainly be in place to touch base with them again and again.On top of that, be sure you are finding 'why' they called in the first place because your main goal should be to solve their problem before all else as this will inevitably lead to closing deals.

Some potential drawbacks to keep in mind are:Additional closing and loan origination costs (two transactions/mortgages instead of one) - speak to your lender and title company about costsTwo insurance policies instead of one - probably close to double the insurance cost as compared to a duplex - get a quote from a good insurance agent and compareTwo sets of property taxes instead of oneThese certainly aren't deal killers, and the benefits noted above may outweigh the disadvantages.

The cost far outweighs the benefits for that amount of money.

This longer life would negate some of the tax benefits that are afforded to owners of residential rental properties (due to the shorter depreciable life on those types of properties), and would most likely cause your rental income to be taxable more often then not, right?

It's not something I would be opposed to, I actually think there is a benefit to both the tenant and the landlord.  

But, since you don't yet know this tenant, if you want to give the benefit of the doubt, I would give them a letter that says: if they don't pay the September rent by Monday, you are evicting.  

My main concern at starting all this is talking to people.

My main question here is do you have any tips on how I should approach the tenant/situation if they refuse to open the door.

My main question is should I pay off my debt before looking into investing?