The deduction for mortgage interest in this case would indeed be $33,750.Regarding your second question about the origination years of the mortgages, the limitation on mortgage interest deductions generally applies to new loans taken out after December 15, 2017, for both single filers and married couples filing jointly.

If you are married, try leveraging your wife's intuition on this a bit.I like to be within an hour or so of our properties so that I can manage them easily myself.

If you're married you can have 10 and your wife could have 10.

Here's scenario:In my early 50's married with 2 kids, good income, live in San Diego, CA.

that gives you some doors.. but I find a lot of folks if they are used to living in a home with a family etc.. moving into a 4 plex and living with their tenants is a non starter.. although for singles and newly married seems to work OK. 

My wife had already remodeled the kitchen, and after we got married, we spent some time to clean it up and do a full bathroom remodel. 

My fiance and I are looking to purchase our first home together. I am not a first-time homebuyer and he is. With our income combined we can afford the homes in our area and further out, however separated we can't. I w...

Got married in 2002 and have rented both units ever since.

Also you can still get the 250k limit even if you don't qualify for the full 500k married filing jointly.

While you are not married, you may need an attorney to break up here, so it's close enough.