It's a good time to start exploring your loan options and setting yourself up to search alerts so that you can become familiar with the area, and start running the numbers :) it's a little harder to cash flow in the north side, but the appreciation is quite significant. 

It’s a simple strategy that can pay off big in the long run.

You can easily do this on a spreadsheet, and it will take less time to track than finding and learning new software.

I can absolutely see an argument against it.

So if you can collect rents into your business either by deeding the properties to your LLC (be careful of the due on sale clause on your mortgages) or by signing a master lease between you and your LLC and having the LLC sublet then that may help.

Worst case you can transfer the money from the current custodian into Fidelity and back and forth it would just create work for you and possible wiring fees....

This way you will be able to compare contractors' estimates, which can vary widely.

Also the majority of those costs to covnert to a 2nd unit will need to be capitalized and depreciated, but some things (new appliances, flooring, paint, kitchen cabinets) can be shorter year assets vs. across the full 27.5 and IF it turns out that unit is > 50% you can use bonus as well on those items.

First get a job.Save enough for 3.5% down for FHA mortgage and buy a 2-4 family property.You can live in one unit and rent out the rest.

One way this can happen is if there were two tenants on the lease - the check should be made out to both of them.