Most lenders have seasoning requirements, so you would need to own the property for 12 months to obtain a loan based on appraisal rather than lower of appraisal or purchase price.The longer the period of since property purchase the more likely an appraisal higher than purchase price.The exception may be a "hot" market where prices are moving up sharply almost every day. 

I'm analyzing deals every day just to practice analyzing and finding cash flow in my area looks promising.

Initially he started doing is own bookkeeping and after his 2nd deal he said " If you can help us everyday, I will take your challenge to cover your fees and you and your firm can be our CFO"Challenge - Buy 5 properties and sell or rent at least 4 in the first month.

Investors go wrong this way every day.

But if you’re not doing it every day, and haven’t done lots of transactions, and aren’t intimately familiar with the local market on a house by house level, then you couldn’t possibly know as much about things to avoid and best practices etc. as someone who does it every day for a living and has done lots of transactions.

That is not scientific at all and would be a pain to look at every day to see if there are short term bookings.   

May be worth a meeting and a conversation to sound them out.Edit for a fun story:I worked with this guy who was super stoked on 420, had "legalize it" stickers all over his car, wore Bob Marley shirts, stopped work every day at 4:20 to take a hit, etc.

Using antifreeze instead of water keeps it from smelling if you aren't able to check it every day.

I think this tenant is starting to come across as high maintenance and this was just another thing piled on top of other things.Nearly every day she has asked me to do something. 

CLAIM THOSE ALL DAY EVERY DAY!