I started Selling houses in College and was making good dow, and started working with a investor house he flip I got the listing, So boom I had it made, Finally it was last year in school, He died and I have sold over 36 homes in San Diego La Jolla Market avrg. price was $1.5M so no pocket change commission it was nice for a 22 year old,  made really good money, but had nothing to show, Just cars and clothing and few rolexes. 

As that worsens over the coming years as baby boomers retire, your taxes will only go up more.

One of my bigger internal conflicts was that I've had to use some cheaper maintenance, rehab, appliance, service, etc. options over the years to save money when I was starting out, but I would do my best to facilitate the work to make sure quality & service for my tenants were still good.At the same time sending out christmas gifts, painting murals at my expense for the community, taking 6 days of personal days at my job to assist a tenant through permits/licenses/court hearings, coordinating with attorneys and consultants to help a tenant navigate his business, baby/newborn gifts, and numerous other activities over the years to just make sure I'm there for my tenants whether or not they asked.

I came from family owned horizontal projects, I hate starting from scratch, but baby steps to financial freedom, we need to start somewhere. :)

Unless there is an instant family on the way and you absolutely need more space (even with a new family a 2-bdrm cottage is sufficient - babies do not need much space in the first year).Why not stick it out in the present house for another 1-2 (or maybe 3-4 when your finance has finished university) years and pay down more of your debt (student loans and mortgage) to put yourself into a stronger position to acquire investment properties.In the interim, you could further educate yourself on real estate and start to narrow the gap on selecting the type of investing that best fits your lifestyle and ambitions.

Medical care is poor in Saipan, so they came to the US to have the baby.

If I need a respray within 6 months, it's only $75 (not bad).I have a feeling I am going to run into a language barrier issue- one side is Hispanic and speak very little English, and there are quite a few things that the tenants have to do to prepare for tomorrow (dry all their clothes, vacuum, etc.) and I'm worried they won't listen to my wife and the treatments will be useless.

Starting to realize house hacking a quad may be a pipe dream with a baby (and 2nd in the near future) due to layout/square footage issues.To your comments;]1) Rent being BEST case scenario; in this market do you foresee rents decreasing?

That later emanated through everything when I moved in and contaminated all of my clothes/belongings so I was slightly frustrated of not being told that.

Also check if they have a dryer that it's properly venting outside.. and that she's not leaving wet clothes to air dry in the house...No house plants or fish tanks... as the extra moisture they need only adds to the problem