I personally don't think tiny homes are going to be popular for the long term.

Even with LLC, can I still do taxes in 1040 Schedule E?

question, best practice is to put it on Sch E if you own it, Sch C if you don't.

Older homes in my area are in some cases in very popular parts of town and appreciate greatly.

Some more popular than others.I definitely would not offer anything close to 210k they are asking for as having seen it first hand, and talked to tenants about problems,  there is PLENTY of work to be done to get it up to AirBnB standards.  

Any breach will result in immediate eviction.Otherwise, I hope you have a new tenant lined up, or you're prepared to deal with the revenue loss from a vacancy and possible PR issues if his business is especially popular in the community.Good luck!

If restaurants and bars stop to pop up in these neighborhoods that are popular with 20 something northsiders my bet is that these communities will benefit from a population shift of Gen Yers south and west who are intent on keeping housing costs low to stay in the City.

Yellow is the most popular, so maybe doing a pink or orange or green will help your piece stand out in the crowd.

If you are looking to handle your applications, screening, and lease e-signing from one place, it might be worth checking out. 

Ideally, I am looking into automated/e-payment methods such as Zelle.How do you collect your rents?