My fear was more on the appreciation side of things due to a higher priced property in a currently booming market.

I'd recommend writing an offer a day until you get comfortable being rejected, then you'll get over your fear of offending people.

As Buffet says, "Be fearful when others are greedy and greedy when others are fearful.

When others are greedy be fearful, when others are fearful be greedy 

Similarly, whether the market is likely to appreciate/ hold steady / depreciate would also be important considerations...obviously, you'd approach a seller in a tiny dead town differently than a seller in a thriving city with 25% appreciation....we don't know if these properties are in the middle of Kansas or the middle of Manhattan, which makes it difficult to zero in on the best strategy....what others mentioned about patience could be a good strategy in some markets, but patience might not a good strategy if there are thousands of other buyers circling around...Also, the finances, priorities, goals and fears of the seller would be important factors to help you determine the best approach...for instance, a seller with little equity, poor cashflow, no appreciation, tons of impending capex bills, and bad tenants would obviously be a different deal than a seller with all properties paid off, excellent cashflow, excellent appreciation, no capex projects on the horizon, and A+ tenants. 

There will always be a reason to wait a little longer, but I think it is a mental block caused by fear of the unknown.

There is always a fear of the unknown when moving forward with any investment opportunity especially if you have never worked with the lender before.

I fear that people are trying to request showings but there's some type of disconnect in the process.

I would love to use the BRRR strategy but I have fear about not having the capital to fund rehabs myself as well as putting down the down payments for hard money lenders.

When I would bring these complaints up with the cleaner, she would generally deny the allegations or make excuses, and out of fear that I wouldn't be able to find someone else (or just putting my head in the sand and avoid the problem all together), I would defer to her and not push the issue.