I'm looking for a way to collect rent in a more automated way, but also keep track of the information of who has paid and when (While keeping in mind my tenants are C/D tenants). 

I think a more reasonable area is Dorchester and Quincy, in terms of value. 

One thing I would like to add, and take it for what it's worth, is the title of your post....you need a more positive attitude.

Having an understanding of rental properties and first hand knowledge of AirBnB will help make you a more well rounded appraiser.

There will propabaly be investor qualifications (accredited or sophisticated) but it’s a great alternative that allows folks who want to get out of a participation (hands on) ownership role and 1031 up into a more risk averse large MF building while being hands off.The sponsor will take fees of course like a normal syndication (most likely) and the returns may be slightly less, but you should still share the appreciation rights and ultimately just continue to 1031 up and up.Happy to answer questions.  

I was wondering if anyone who has done this can tell me if after comparing price per sqft of the building aspect of the project only (cost of land, environmental remediation, and demo excluded) they have found modulars to be a more cost effective way to go rather than stick built.

Not knowing your local market but I would guess $150-200/sf is a more realistic number but it will vary depending on what your specific needs are. 

A more specific example is if a private investor had 135K in the deal for me to obtain the property, and I made a monthly payment to that investor for 12 months with the intent to cash out refi and pay the remainder of the 135k plus reasonable ROI... does this seem typical or is it all based on investor objective?

Our tech scene may not yet truly rival that of the Bay Area, but the California markets are quickly pricing themselves out of some promising young talent - talent that has started looking east for lower overheads and a more dynamic, inclusive, culture.

Are there sites other than AirBnB and VRBO that you would recommend that have a more extensive screening process?