U know the Pad split craze although I suspect neighbors would not like it.. but with the parking etc.. might get premium per room rents ??? 

Rent would probably be a short term nightly basis. 

I have additional questions but am running short of time drafting this post.

Collateralized Private Loan – Some private money lenders (PMLs) may allow you to pledge one of your properties as collateral for a short-term loan. 4.

Wholesaling is a great low cost way to make a lot of short-term cash, but it does not build long-term wealth.

It's my understanding the Gator Method consists of providing short term loans to cover other investor's earnest money deposits.

I mention all this to in short say, expect very high maintenance on the front end. 

Everything comes with a risk but I want to hear everyone's opinions for both states in the long run, thanks in advance It really depends on your style and goals and type of investing.I invest in multiple states and there can be some substantial differences.First decide if you want to do Flips, Long Term Rentals, Short Term Rentals, Shared Housing, Multi Family, Land, Tax Deeds, REITs, Syndication, Commercial and then decide. 

@Matt Schreiberi think the short answer is... no.but... a lot of inputs missing - which market? 

Also, the short answer to your question IMHO is as early you possibly can haha