I would second comments of Ben, VISIT properties, winter season is best time in states where it is snow (East/Midwestern states), I'm finding poorly managed investors, poorly managed flips or owner occupants are desperate to sell at any reasonable price.  

yes, we were hoping to have at least one vacation/short term rental as Pasadena in particular has really high short term occupancy rates and some high peak seasons.  

Best to talk to some seasoned investors and then figure out exactly what areas fit your budget and level of risk.Dave

Interesting that your rentals fetched more as a LT rental than a vacation rental during the school season.

I love hearing the feedback and methods from people in the same shoes as me and from someone like @Jay Hinrichs who is a seasoned vet and we can learn from him

I would move out of my current home and live in 4-plexCurrently living situation is SF homeMortage - 1,000 (with HOA and rounding up on mortgage)Potential Rent - 1350 (1300-1400 low to high season)Likelihood of renting w/in 45 days - 70%Potential 4-plexselling price - 220,000 (would only do deal if they would come down to less than 215,000)3 occupied/1 vacant rent - 550 on month to month (1,650 p/mo);  current tenants are long term tenants;  rental market calls for 750-800HOA - optional at 360 p/moWould purchase with 5% down ( 10,750)I would do a 15yr loan to pay it down soonerAppraisal is probably 230k.

After $300 a month for your mortgage payment and $600 a month lot rent, you have a property that could likely rent for ~$200 a night during peak season (based on a quick glance at similar properties on Airbnb).

Having sad that the reason, I think you should seek out a fund and more importantly a seasoned fund manager is really 3 fold:It allows you to get into bigger deals than you could do on your own.  

or will that only create more headache than help come tax season?

You can read the whole article here: https://www.mba.org/2017-press-releases/january/mortgage-applications-decreased-over-two-week-period-in-latest-mba-weekly-surveyWhat does seasonally adjusted basis mean?