It's tiresome reading the "advice" of many of the BP crowd - can tell quickly:1) Who has tons of advice, but litte actual experience2) Who has some experience, but obviously "don't know, what they don't know"3) Who has a lot of experience, but limited exposure, and can't think past their "noses"The ones that have been there & done that, and can have a broad understanding to offer sound advice - are not plentiful:(

Yes you can if you meet the requirements.If you are not a real estate professional, the passive activity losses (PALs) generally are deductible only (1) against income from passive activities, (2) when the entire interest in a passive activity is disposed of in a taxable transaction, or (3) under the $25,000 rental loss privilege for qualified rental activities (subject to the $100,000 AGI phase-out).The general is a rule allowing up to $25,000 of active participation(see below) rental real estate losses as a deduction against nonpassive income.The taxpayer must make management decisions with regard to the property, have at least a 10% ownership share in the property, and the cannot be a limited partner.

So, I'm looking to limit the amount of stress. 

A “pass-down” lease refers to the current tenant essentially signing over their lease to the next tenant, and if your property is in-demand, encouraging this can limit vacancies and create student appeal.Consider demand when determining rent prices.The beauty of real estate investment in a college town is stability in rental prices.

With the limited information, I don't see how that can be feasible.

Is there a time limit to pay it back if I have to.

However Boulder County still allows nightly rentals, for now at least (with some restrictions such as needing a license and limits on the number of nights per year).

My rent is $1,750/mo, but I think their limit is $5K.

I see that Oahu basically requires you to be in one of a limited list of properties or condo buildings.

After getting quotes back from my broker, I am being told its actually 25% down and the best rate on a non-owner occupied investment property at this time is 4.125% with a limit of 4 units total.