The question I have is should I use my personal name in the letters or use a company name with logo and website?  

Congratulations on your first successful investment! 

Sound like you are positioned for major success @Christopher Toth !

My painter works for a painting company but does side work on his own and often when the company has a break between jobs.

If I choose to hire a cleaning company I will need to log my hours and have the cleaning crew bill per hour so that I can prove I that I am working at least 100 hours/year *and* that my time spent is more than anyone else (so in this case, my hours must be more per year than my cleaning company).Some more details:https://www.hwcpa.com/passive-...

Many OOS investors set themselves up for failure because they don't invest the time to ACTUALLY understand:1) The Class of the NEIGHBORHOOD they are buying in - which is relative to the overall area.2) The Class of the PROPERTY they are buying - which is relative to the overall area.3) The Class of the TENANT POOL the Neighborhood & Property will attract - which is relative to the overall area.4) The Class of the CONTRACTORS that will work on their Property, given the Neighborhood location - which is relative to the overall area.5) The Class of the PROPERTY MANAGEMENT COMPANIES (PMC) that will manage their Property, given the Neighborhood location and the Tenants it will attract - which is relative to the overall area.6) That a Class X NEIGHBORHOOD will have mostly Class X PROPERTIES, which will only attract Class X TENANTS, CONTRACTORS AND PMCs and deliver Class X RESULTS.7) That OOS property Class rankings are often different than the Class ranking of the local market they live.Class A is relatively easy to manage, can even be DIY remote managed from another state.

Chicago Property Management, Chicago Property Managers, Chicago Property Management Company | Straight Up Chicago Investor Podcast

Deeds to burial sites, certain transfers of ownership in real estate companies and farms and property passed by testate or intestate succession are also exempt from the tax)There should be no taxable event unless a sale occurs or when your dad passes.At that point, you should receive the property at the stepped up basis as the life estate is null due to the death.This is tricky - it will depend on how the deed is held.You should check with the attorney who made the initial change and check with your CPA once you find the answers from said attorney.

Given this is your first investment endeavor, I would highly recommend going with an experienced and reputable management company that will mitigate your risk when the not-so-fun parts of property management arise.

They are property owners in your neighborhood, not an external company with no stake in the community other than management fees.