Hi Jacob,I agree with Bruce, if you can show up or call the HOA to find out their stance on 30 day rentals this would help you figure things out better.Ask to see the HOA's Bylaws and CC&RRs (Combined Community Rules & Regulations) to see if there is language that allows rentals/leasing (without restriction).If there is, determine what the criteria is for amendment changes to the CC&RRs.

G'Day Carlos,Personally, I think it's a recipe for disaster rehabbing from out of state.IMO you would need deep roots in the specific market you are looking at investing.Or years long experience of knowing the who, what and when in that specific market.I only know of a handful of folks that can do it successfully and even they have been at it for many years and probably still loose money on rehabs to this day, no matter how integrated they are with everything and everyone.A good resources for pre-purchase, during rehab and after rehab's is Inspectify.Always get eyes on site before buying a property or processing a progress draw for the rehab.Much success

Definitely look into STR regulations in any area you're researching.

Since the start of the year, I've read a handful of BP books:- Rental Property Investing (Brandon Turner)- How to Invest in Real Estate (Brandon Turner/Josh Dorkin)- Investing in Real Estate with No (and Low) Money Down (Brandon Turner)- BRRRR (David Greene)- Multifamily Millionaire Volume 1 (Brandon Turner/Brian Murray)- Start with Strategy (Dave Meyer), currently readingI was thinking of using the equity to BRRRR small multifamily properties and combine some concepts from both the BRRRR and Multifamily Millionaire books (specifically making cash offers via HELOC to secure distressed properties, ideally vacant to set market rents).

Also, be sure to read up on the new laws hitting Colorado Specifically.

Also, based on the new regulations (1 of the 2 units must be owner-occupied), how do you think this will impact the home's value?

As far as the lender goes, if I'm buying properties that qualify for conventional loans does it really make a difference if I build up a relationship with a specific bank vs just shopping around each time I buy a new property?

Property management is a pretty painful industry similar to general contracting... no one ever calls to tell you how grateful they are that the heat is working lolHere in Illinois, the answer is yes or you at least need to have a managing broker on your team as JW mentioned above. 

Mostly he's interjecting opinion about an industry he doesn't know intimately. 

Currently I have only rehabbed our home but I believe that I could do more in this industry.