I am about 6 months away from getting my architecture license.  

Ended up graduating from college of architecture at GA Tech.

I'm from the Boston Ma area and I currently have my bachelors in architecture with three years in residential (anything from new construction to any size addition) and currently working in commercial architecture (doing anything from 20 unit townhouses to hotels, large residential units, retail, biomed, schools, and more) while still doing residential on the side.

Structural aspects and Engineering behind the architecture.

Here are a few things that will give you a very good idea of how well it's been maintained and updated working from the outside in:Roof - if you have architectural or composition shingles it will likely be more updated then a house with 3 tab shingles.

Would you recommend a certain architecture/design software for people who do not have a lot of design experience and really just need it for more basic building permit proposals?

An article below for everyone's benefit.http://www.cleveland.com/architecture/index.ssf/2017/10/cleveland_is_growing_from_insi.html

IF (using hypothetical numbers here) you're building a townhome for $250K and it's worth 500K in NY (unsure where in NY the home is), then I would say try to get funding via construction or private loan to (1) pay off the back taxes and (2) secure a developer who can do everything (architectural drawings, permits, build the house, etc). 

Most cater to young professionals who want to live in SFH's with some historic architectural elements vs living in an apartment. 

I got my Master of Architecture degree and I use my design skills daily.