I attend regular meetup in Mtl and one of the meetups entails remote investing in the USA.

A good agent will still manage the entire transaction and coordinate inspections/repairs which is particularly important since you aren't in town.I'm not sure about what closing costs entail in other states but here in Western NY the seller is responsible for their attorney's fee, transfer tax (either $4/1000 in Niagara County or $9/1000 in Erie County), property tax which is prorated to the date of acquisition, search and survey, documentation preparation and recording, repairs according to what was found during the appraisal, town inspection and any judgement or other assorted liens against the property. 

The numbers may seem juicy but I can tell you the fact that you need to change the septic may entail more maintenance then it appears.

Would you mind telling me what bird dogging or wholesaling means/entails?

Find out specifically what you need to do to "prove" yourself and also make sure you get a clear understanding of what your position will entail. 

I would encourage the sellers agent to be more assertive if possible with the situation.

Going with someone experienced may entail taking the syndication route and becoming an equity partner in someone else's deals.

Challenges can stem from (1) the implementation process [this entails customizing your settings, migrating data, setting up your accounting / banking structure, etc - be weary of software companies that don't have a process for this] (2) learning a new system (3) inexpensive cloud based software often does not have the security infrastructure in place to adequately store your financials, owner information, tenant information, etc.In my experience, the answer to your question is dependent on what your short and longterm goals are. 

Most of "THE" states will file suit with states rights assertions. 

@Robert Glennon, the only thing that glared out to me is: can you PROVE your assertions when it comes to say, a Tax audit?