Thank you all for your responses. I will take your comments into consideration so that I do not make this decision based off of emotion and hate for a long commute everyday.
@Joe P. I have housed hacked before and had several "short term ish" military roommates before AirBnB or other vacation rental websites were popular. So besides leaving valuables at my parents house I would be comfortable with having strangers in my home. And so far my math is working out that mortgage, HOA, taxes, insurance, and possible maintenance comes out to about $750 which I can definitely handle if I do not make anything on this STR. If the place were to rent out every weekend I would be at my parents place anyways. I have thought about doing a house hack as well, but the one bedroom condos I'm looking at are around $80,000 and the 2 bedrooms are around $250,000, so I would hate to eat up all of my capital available and miss out on a possible multifamily that I could try to purchase this summer (I'll keep looking for a deal even if I do this condo!). I have also thought about a single family home, but of my previous deals the only one that did not cash flow is my only single family, and finding one in Omaha in a decent area is difficult. I guess I was thinking that perhaps I could live in this condo for a year or so during the week and STR on the weekends, and then switch to either full time STR or a long term lease for $850-$900.
@Julie McCoy I would be at my parents farm on the weekends anyways, but this would shave an hour of my drive each way to work and about 100 miles total off my vehicle each day. I understand that most months I would not make a lot of money, if I could come close to breaking even I would be happy (I think $100 a weekend during an off month is a reasonable expectation for downtown Omaha) and then during Berkshire Hathaway shareholder meeting in May I think I could easily make over $1,000 and then over $2,000 during June and the College World Series (my condo would be a long walk or short cab ride to both events).
@Jimmy Dudley I know this is not a cheap option, hence why I reached out to you guys as the experts! I have been looking for three months now and made several offers but it seems that all of the multifamily homes are either in real bad parts of town, or the owner won't budge from a very high listing price. I will definitely keep looking though, even if I do decide to put some of my capital into a condo. That's a great idea to look around for farms with multiple dwellings, even if it was something like an old farm house with a smaller farmhand quarters I could make that work. But this would likely not solve my commute problem, and farms and acreages are way overpriced around here (growing up on a farm I can speak to this!). I think I would be able to deal with an hour commute better if I was on the coast, but being that I am driving over 50 miles each way in a truck I am getting tired of this drive (commuter car that I had was just totaled). And I have already listened to all of the BP podcasts, so that only solves about an hour a week of my commute.